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    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:to="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_019fdcb3-18ff-7acb-8fff-30cfec44eb82_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_019fdcb3-18ff-78eb-aba3-bf7d5c1c5720_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract asset after allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerAssetNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetNet" xlink:to="lab_us-gaap_ContractWithCustomerAssetNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_019fdcb3-18ff-75f3-a167-02396346dda7_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance and premium payables</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_019fdcb3-18ff-7c84-8a5f-87a3332ab084_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds at Lloyd's</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Lloyd's Funds</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Lloyd's Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_019fdcb3-19df-7c7d-8a81-631d01f10813_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinate Debt Due 2039</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039 [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:href="skwd-20260930.xsd#skwd_UnsecuredSubordinatedNotesDue2039Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:to="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TrancheBDDTLMember_019fdcb3-1978-7cf9-a1b4-dac619695168_terseLabel_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche B DDTL</link:label>
    <link:label id="lab_skwd_TrancheBDDTLMember_label_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tranche B DDTL [Member]</link:label>
    <link:label id="lab_skwd_TrancheBDDTLMember_documentation_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tranche B DDTL</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TrancheBDDTLMember" xlink:href="skwd-20260930.xsd#skwd_TrancheBDDTLMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TrancheBDDTLMember" xlink:to="lab_skwd_TrancheBDDTLMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_019fdcb3-18ff-7ab2-bd68-096c3794a29a_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Investment in Debt and Equity Securities, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease_019fdcb3-1873-7c81-b226-e97a47137dff_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period provision for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Allowance for Credit Loss, Period Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_019fdcb3-19df-7e5e-b66b-f1bf504c0a73_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CurrentIncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_019fdcb3-18ff-754f-9bdb-586a91a606e4_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_019fdcb3-1977-7435-8e36-3cfac95662a7_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AlignedSyndicatesMember_019fdcb3-18ff-7d0e-81af-862ce641669a_terseLabel_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aligned Syndicates</link:label>
    <link:label id="lab_skwd_AlignedSyndicatesMember_label_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aligned Syndicates [Member]</link:label>
    <link:label id="lab_skwd_AlignedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Aligned Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AlignedSyndicatesMember" xlink:href="skwd-20260930.xsd#skwd_AlignedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AlignedSyndicatesMember" xlink:to="lab_skwd_AlignedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_019fdcb3-1978-7bc9-80d8-83e767b720bf_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_019fdcb3-1873-7891-97ba-fc30efc312b2_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_019fdcb3-1978-778c-a397-02a117d24577_verboseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Indirect loans</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_019fdcb3-1978-7121-9961-3091e9cced18_terseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in indirect loans and loan collateral</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_label_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indirect Loans and Loan Collateral [Member]</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_documentation_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Indirect Loans and Loan Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:href="skwd-20260930.xsd#skwd_IndirectLoansAndLoanCollateralMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:to="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_019fdcb3-1978-7d05-9deb-69886f13653d_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FeeIncome_019fdcb3-18ff-7a1b-9f79-46821cf9242b_terseLabel_en-US" xlink:label="lab_us-gaap_FeeIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting fee income</link:label>
    <link:label id="lab_us-gaap_FeeIncome_label_en-US" xlink:label="lab_us-gaap_FeeIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fee Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FeeIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FeeIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FeeIncome" xlink:to="lab_us-gaap_FeeIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_019fdcb3-18ff-7b0f-8b6f-54592ccf8891_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_019fdcb3-18ff-7f29-bd1a-adb4c527c53a_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:to="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019fdcb3-19df-7764-b6bb-1217e90b5792_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_019fdcb3-1978-78cf-bd25-fb31a3840f7d_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available for sale, gross unrealized losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_019fdcb3-1977-7236-bed9-aeff165ea8da_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, par value (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_019fdcb3-18ff-7152-967a-e3f8c6009a8f_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Gross intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_019fdcb3-1977-777c-9b1e-1bf460954d47_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of reportable segments</link:label>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Reportable Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfReportableSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NumberOfReportableSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfReportableSegments" xlink:to="lab_us-gaap_NumberOfReportableSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock_019fdcb3-1977-7ace-986f-0633aeb9bd5e_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Derivative Instruments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Derivative Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfDerivativeInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fdcb3-18ff-7b4d-81cb-26bb2d2b94c3_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fdcb3-18ff-7335-b39b-6dde130a9393_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
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    <link:label id="lab_dei_EntityAddressCityOrTown_019fdcb3-18ff-7952-8813-5dccd641629f_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount_019fdcb3-19df-72bd-aa2f-0cc405e874a7_terseLabel_en-US" xlink:label="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share repurchase program, additional authorized, amount</link:label>
    <link:label id="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount_label_en-US" xlink:label="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share Repurchase Program, Additional Authorized, Amount</link:label>
    <link:label id="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount_documentation_en-US" xlink:label="lab_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share Repurchase Program, Additional Authorized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount" xlink:href="skwd-20260930.xsd#skwd_ShareRepurchaseProgramAdditionalAuthorizedAmount"/>
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    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeNet_019fdcb3-18ff-707e-83e7-ea522549ba06_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeNet_label_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Fair Value, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeFairValueOfDerivativeNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:to="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesAbstract_label_en-US" xlink:label="lab_us-gaap_ReceivablesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Receivables [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivablesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReceivablesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReceivablesAbstract" xlink:to="lab_us-gaap_ReceivablesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AndrewRobinsonMember_label_en-US" xlink:label="lab_skwd_AndrewRobinsonMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Andrew Robinson [Member]</link:label>
    <link:label id="lab_skwd_AndrewRobinsonMember_documentation_en-US" xlink:label="lab_skwd_AndrewRobinsonMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Andrew Robinson</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AndrewRobinsonMember" xlink:href="skwd-20260930.xsd#skwd_AndrewRobinsonMember"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_01a1a767-7349-72cf-b314-1c6494b4a3c5_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net, ending balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019fdcb3-1977-7761-a519-581be8721a2f_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incurred, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
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    <link:label id="lab_us-gaap_ProceedsFromStockPlans_019fdcb3-18ff-7b51-8641-67ed790ee27b_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from issuance of common stock</link:label>
    <link:label id="lab_us-gaap_ProceedsFromStockPlans_label_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Stock Plans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockPlans" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromStockPlans"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromStockPlans" xlink:to="lab_us-gaap_ProceedsFromStockPlans" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnVsPeerGroupTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:to="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonRule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LicenseMember_019fdcb3-18ff-73f9-abfc-99f5d2c2bc3e_terseLabel_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Licenses</link:label>
    <link:label id="lab_us-gaap_LicenseMember_label_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">License [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LicenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LicenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LicenseMember" xlink:to="lab_us-gaap_LicenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherExpenses_019fdcb3-1978-7f5c-bdb0-44470584a2f8_terseLabel_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other expenses</link:label>
    <link:label id="lab_us-gaap_OtherExpenses_label_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherExpenses" xlink:to="lab_us-gaap_OtherExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_019fdcb3-1977-7abd-9d4c-f2559ad6cec2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue_019fdcb3-1873-7e20-8713-31984a3aee70_terseLabel_en-US" xlink:label="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Securities held as collateral, at fair value</link:label>
    <link:label id="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue_label_en-US" xlink:label="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Securities Held as Collateral, at Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuritiesHeldAsCollateralAtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:to="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CaptivesMember_019fdcb3-1978-7ead-8ddb-5e3a8ea21c20_terseLabel_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Captives</link:label>
    <link:label id="lab_skwd_CaptivesMember_label_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Captives [Member]</link:label>
    <link:label id="lab_skwd_CaptivesMember_documentation_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Captives</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CaptivesMember" xlink:href="skwd-20260930.xsd#skwd_CaptivesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CaptivesMember" xlink:to="lab_skwd_CaptivesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_019fdcb3-1977-7c1d-8964-c5ecb045d3ab_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee income</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019fdcb3-19df-7a62-b146-c7f80e21cbd2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_019fdcb3-1977-7f62-a50c-0ba25e1488e5_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_019fdcb3-1978-7f48-9d75-2a9d8f2d5e70_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Municipal securities</link:label>
    <link:label id="lab_us-gaap_MunicipalBondsMember_label_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Municipal Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MunicipalBondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UseOfEstimates_019fdcb3-1873-7b9d-8442-9643f8cf16a4_terseLabel_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Use of Estimates</link:label>
    <link:label id="lab_us-gaap_UseOfEstimates_label_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Use of Estimates, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UseOfEstimates" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UseOfEstimates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UseOfEstimates" xlink:to="lab_us-gaap_UseOfEstimates" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_019fdcb3-1978-711a-897b-f4aaed7d848b_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related and Nonrelated Parties [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionsByRelatedPartyAxis"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019fdcb3-1978-74e1-a288-1873db4253dc_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (loss) income, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_019fdcb3-18ff-7a7f-846b-9bf95ba56c30_negatedTotalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss"/>
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    <link:label id="lab_skwd_StrategicPartnerSyndicatesMember_019fdcb3-19df-79ed-b607-df3ab4aa6e25_terseLabel_en-US" xlink:label="lab_skwd_StrategicPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Strategic partner syndicates</link:label>
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    <link:label id="lab_skwd_StrategicPartnerSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_StrategicPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Strategic Partner Syndicates</link:label>
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    <link:label id="lab_skwd_SPA1925Member_019fdcb3-19df-7c6d-b841-31456d4f7d69_terseLabel_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SPA1925</link:label>
    <link:label id="lab_skwd_SPA1925Member_label_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SPA1925 [Member]</link:label>
    <link:label id="lab_skwd_SPA1925Member_documentation_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SPA1925</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SPA1925Member" xlink:href="skwd-20260930.xsd#skwd_SPA1925Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SPA1925Member" xlink:to="lab_skwd_SPA1925Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_019fdcb3-18ff-7fc3-ab88-e608b243bb9b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Face amount</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_019fdcb3-18ff-75c8-8d43-4720ec39e54b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, term</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTerm" xlink:to="lab_us-gaap_DebtInstrumentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_019fdcb3-1900-7bf3-8eb3-6a4a968b1f7d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_019fdcb3-1977-77d2-9e47-a588c38e996c_terseLabel_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retail</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RetailPortfolioSegmentMember" xlink:href="skwd-20260930.xsd#skwd_RetailPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RetailPortfolioSegmentMember" xlink:to="lab_skwd_RetailPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_019fdcb3-1873-7f94-9a88-276a2212528d_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_019fdcb3-18ff-7592-91e5-d35777fdf9fe_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019fdcb3-1900-7baa-adc7-4d5cc6248b56_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_019fdcb3-1977-7b5c-92c8-8d181821bf88_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsDomain_019fdcb3-1977-7563-b0ca-b84c43b12525_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:label id="lab_srt_ConsolidationItemsDomain_label_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsDomain" xlink:to="lab_srt_ConsolidationItemsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_019fdcb3-19df-7cfe-993a-9512609ae303_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_019fdcb3-1977-7fbc-ad27-0ac8afa1061b_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Per share data:</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_019fdcb3-1977-76a4-a5c2-40b96415c70f_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_019fdcb3-1977-764a-a263-2da76f2732dc_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_019fdcb3-1977-703d-a3ce-6e865c54c0d0_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_019fdcb3-1900-757b-a918-427385dd56a1_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fdcb3-18ff-7218-b781-9be611b70dfd_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $5,910 and $7,000, respectively) (amortized cost of $2,265,283 and $1,848,755, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fdcb3-18ff-7506-ada6-e63e3d5dbf98_netLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fdcb3-18ff-75ea-9c08-c0e36e906063_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fdcb3-18ff-7caa-9877-0bee9382c919_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019fdcb3-19df-7e03-99be-ec625351e640_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases (sales) of property and equipment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:to="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019fdcb3-18ff-788b-8d5e-5d523d7136f2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Preliminary Purchase Price Allocation</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired and Liability Assumed [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureName_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureName_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureName" xlink:to="lab_ecd_CoSelectedMeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss_019fdcb3-1977-7f42-8940-8437da2d7452_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total unrealized gains (loss) for the period recognized in accumulated comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Other Comprehensive Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_019fdcb3-18ff-7ce0-99b3-f2e461e8779c_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment and Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019fdcb3-18ff-7208-91a6-b15f2233c43f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA2Member_019fdcb3-18ff-7685-b8d9-5b989d7ae157_terseLabel_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SMA2</link:label>
    <link:label id="lab_skwd_SMA2Member_label_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SMA2 [Member]</link:label>
    <link:label id="lab_skwd_SMA2Member_documentation_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SMA2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA2Member" xlink:href="skwd-20260930.xsd#skwd_SMA2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA2Member" xlink:to="lab_skwd_SMA2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_019fdcb3-19df-7327-a73c-8b2e5cd91c58_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance and premium payables</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Reinsurance And Premium Payables</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Reinsurance And Premium Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_019fdcb3-1977-7cc6-aafd-d1cd214de899_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, covenant, limitation on additional indebtedness maximum</link:label>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_label_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Limitation On Additional Indebtedness, Maximum with a Debt Balance</link:label>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Limitation On Additional Indebtedness, Maximum with a Debt Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:to="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage_019fdcb3-18ff-7a57-8456-5ae1df83c0cd_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, commitment fee percentage</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Commitment Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditFacilityCommitmentFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:to="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityDomain_019fdcb3-1977-7330-bfa9-f97d87bfe13b_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityDomain" xlink:to="lab_us-gaap_CreditFacilityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fdcb3-1977-7efa-96bb-142d07817c76_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fdcb3-1977-79a2-88d1-dc58d5d56614_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fdcb3-1977-784e-9664-b6f0d646b0a9_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019fdcb3-1977-7357-9c83-496fc3365432_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operating activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SalesCommissionsAndFees_019fdcb3-18ff-74cd-b844-317969744b21_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_SalesCommissionsAndFees" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee expenses</link:label>
    <link:label id="lab_us-gaap_SalesCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_SalesCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sales Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SalesCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SalesCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SalesCommissionsAndFees" xlink:to="lab_us-gaap_SalesCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember_019fdcb3-18ff-79ef-80fb-125c58068a16_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1969</link:label>
    <link:label id="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember_label_en-US" xlink:label="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1969 - Lloyd&#8217;s Specialist Syndicate [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1969 - Lloyd&#8217;s Specialist Syndicate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:href="skwd-20260930.xsd#skwd_Syndicate1969LloydsSpecialistSyndicateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:to="lab_skwd_Syndicate1969LloydsSpecialistSyndicateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote</link:label>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_label_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EquityValuationAssumptionDifferenceFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:to="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_019fdcb3-1977-72cc-bd77-4cec9ed2cf3f_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Fair value of net assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired to Liability Assumed, Excess (Less)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_019fdcb3-1978-7266-880a-002a7fa86a18_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Investment Income</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeTextBlock" xlink:to="lab_us-gaap_InvestmentIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_019fdcb3-1873-7407-a924-9f5bd70f4108_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized gains</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:href="skwd-20260930.xsd#skwd_GrossRealizedInvestmentGainsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FeebasedServiceExpenses_019fdcb3-18ff-7a4f-a449-633b48875667_terseLabel_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fee&#8209;based service expenses</link:label>
    <link:label id="lab_skwd_FeebasedServiceExpenses_label_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fee&#8209;based Service Expenses</link:label>
    <link:label id="lab_skwd_FeebasedServiceExpenses_documentation_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fee&#8209;based Service Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FeebasedServiceExpenses" xlink:href="skwd-20260930.xsd#skwd_FeebasedServiceExpenses"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_019fdcb3-1977-7877-a05e-14b12118e798_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_019fdcb3-1977-798f-a079-273c32258aa8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_019fdcb3-1977-7e56-b876-9795ce1e7c94_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined</link:label>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_label_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgPredtrmndFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgPredtrmndFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgPredtrmndFlag" xlink:to="lab_ecd_AwardTmgPredtrmndFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnderwritingIncomeLoss_019fdcb3-18ff-76c2-882c-4840b9621b94_totalLabel_en-US" xlink:label="lab_us-gaap_UnderwritingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting revenues</link:label>
    <link:label id="lab_us-gaap_UnderwritingIncomeLoss_label_en-US" xlink:label="lab_us-gaap_UnderwritingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnderwritingIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnderwritingIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnderwritingIncomeLoss" xlink:to="lab_us-gaap_UnderwritingIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_019fdcb3-18ff-700b-92d9-4e3ef69688de_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, measurement input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:href="skwd-20260930.xsd#skwd_FixedMaturitySecuritiesMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:to="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_019fdcb3-1977-7c74-85cf-7ff7fa21b320_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019fdcb3-1977-7e69-9761-bcc32df33798_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019fdcb3-1977-7674-8480-7f949b268b6c_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_019fdcb3-18ff-77cb-9ad2-2b6a6468f72e_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unsecured subordinated notes</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:href="skwd-20260930.xsd#skwd_UnsecuredSubordinatedNotesMember"/>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_019fdcb3-1977-77d5-bbd4-bb1b2f36de68_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective tax rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
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    <link:label id="lab_skwd_AccidentHealthMember_019fdcb3-18ff-721b-99d7-dabf9939d6a6_terseLabel_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_label_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accident &amp; Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentHealthMember" xlink:href="skwd-20260930.xsd#skwd_AccidentHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentHealthMember" xlink:to="lab_skwd_AccidentHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019fdcb3-1977-72a3-ab36-6cd62bd2b099_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted effect of awards (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Share-Based Payment Arrangements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements"/>
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    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_019fdcb3-1977-72b8-ba9e-9f668aa1ba6e_terseLabel_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Residential mortgage-backed securities</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ResidentialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_019fdcb3-18ff-79be-a127-28edd5500d5c_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019fdcb3-1873-742f-9db8-4fc63d110f33_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded losses and LAE incurred</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_label_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:to="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_019fdcb3-18ff-7595-9a08-385075bbe8ee_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_019fdcb3-19df-7306-adde-386ae67b1fd4_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_019fdcb3-1977-72e6-b9a5-a647c87e1ecf_terseLabel_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_label_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment [Member]</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_documentation_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditSpreadAdjustmentMember" xlink:href="skwd-20260930.xsd#skwd_CreditSpreadAdjustmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditSpreadAdjustmentMember" xlink:to="lab_skwd_CreditSpreadAdjustmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019fdcb3-1873-7546-b5f4-deb031274370_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_019fdcb3-18ff-7629-9191-f01679f61a4c_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in less than one year</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_019fdcb3-1978-714c-a816-3f4134428fcc_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired to Liability Assumed, Excess (Less), and Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet"/>
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    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_019fdcb3-1977-75f0-90a0-61e355308670_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrExpirationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expiration Date</link:label>
    <link:label id="lab_ecd_TrdArrExpirationDate_label_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Expiration Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrExpirationDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrExpirationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrExpirationDate" xlink:to="lab_ecd_TrdArrExpirationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis_019fdcb3-1977-7ebf-bfa8-7cdb89a2deea_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Axis]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:to="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_019fdcb3-18ff-7ad6-b431-14db444f2428_terseLabel_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net unrealized gains (losses) on investments</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_label_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Unrealized Losses and Gains on Investments [Abstract]</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_documentation_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Unrealized Losses and Gains on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:href="skwd-20260930.xsd#skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:to="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_019fdcb3-1978-79bb-b870-c6bb75e26fb8_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_019fdcb3-1977-742a-9b2d-def999cfb683_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available for sale, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract"/>
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    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_019fdcb3-1977-7803-9b69-0d22e7a41ba5_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_label_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:to="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_019fdcb3-18ff-73e2-b5a4-b129e7476988_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentFixedRatePeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_019fdcb3-18ff-71fb-b94f-7a27d3a4bc88_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubordinatedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebtMember" xlink:to="lab_us-gaap_SubordinatedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedSyndicatesMember_019fdcb3-1977-704d-8b6b-98c773e99cdb_terseLabel_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Managed Syndicates</link:label>
    <link:label id="lab_skwd_ManagedSyndicatesMember_label_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managed Syndicates [Member]</link:label>
    <link:label id="lab_skwd_ManagedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managed Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagedSyndicatesMember" xlink:href="skwd-20260930.xsd#skwd_ManagedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagedSyndicatesMember" xlink:to="lab_skwd_ManagedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_019fdcb3-18ff-7663-8f31-6e1e62379cb0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuances</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Issuances</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AffiliatedEntityMember_019fdcb3-19df-7d56-9da2-c5458d368ab0_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Affiliated entity</link:label>
    <link:label id="lab_srt_AffiliatedEntityMember_label_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Affiliated Entity [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AffiliatedEntityMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AffiliatedEntityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AffiliatedEntityMember" xlink:to="lab_srt_AffiliatedEntityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtPnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:to="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncomeAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIncomeAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:to="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_019fdcb3-18ff-76c8-8901-b61a13a7bc0e_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Other [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:href="skwd-20260930.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_019fdcb3-1977-77b8-908a-175142d93e48_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted-average common shares outstanding</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share Reconciliation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:to="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_019fdcb3-1873-72cc-bba3-543cf3f8d4d1_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable, net</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Receivable, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_019fdcb3-18ff-7975-b797-c1ed45b8f975_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Security, Excluded EPS Calculation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_019fdcb3-1873-74f2-bf2b-a665d71bc039_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_019fdcb3-18ff-7c4c-bfb9-b152f94ad7a4_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_019fdcb3-1873-74c9-b4ac-863fd4303491_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1969 capacity - with fees</link:label>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_label_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1969 Capacity [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1969 Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1969CapacityMember" xlink:href="skwd-20260930.xsd#skwd_Syndicate1969CapacityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1969CapacityMember" xlink:to="lab_skwd_Syndicate1969CapacityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_019fdcb3-18ff-704a-a694-34485e509ec9_terseLabel_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_label_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P. [Member]</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_documentation_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HudsonVenturesFund2LPMember" xlink:href="skwd-20260930.xsd#skwd_HudsonVenturesFund2LPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HudsonVenturesFund2LPMember" xlink:to="lab_skwd_HudsonVenturesFund2LPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentDomain_019fdcb3-18ff-7c81-9328-e375d3ac8792_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:label id="lab_us-gaap_SegmentDomain_label_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentDomain" xlink:to="lab_us-gaap_SegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_019fdcb3-18ff-7083-a34e-b87aaaf74e69_netLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Notes Payable &amp; Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_019fdcb3-18ff-7a16-beb0-92aff806255d_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt issuance costs</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable_019fdcb3-18ff-76d4-bc59-e534fb219d32_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:to="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoActuallyPaidCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoActuallyPaidCompAmt" xlink:to="lab_ecd_PeoActuallyPaidCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Asset Acquisition, Transaction between Entities under Common Control, and Joint Venture Formation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationAndAssetAcquisitionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:to="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_019fdcb3-1978-79f8-bdce-dfe82db71708_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_019fdcb3-1977-7315-9e0e-61033dbed2fe_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of equity method investments and other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:to="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_019fdcb3-19df-7d11-8317-c8aff982acf9_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stated interest rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
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    <link:label id="lab_us-gaap_StockholdersEquity_019fdcb3-18ff-7202-9077-cb83d3ef8762_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_019fdcb3-18ff-74eb-a487-c46035a27a1e_periodStartLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Stockholders' equity beginning balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_019fdcb3-18ff-73c2-85c3-ce2fd8331b70_periodEndLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Stockholders' equity ending balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_019fdcb3-1978-7c7e-ab05-0b0baa1127b3_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Other Asset, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets"/>
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    <link:label id="lab_us-gaap_AssetsAbstract_019fdcb3-1873-7cd9-818e-52269728fde7_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued_019fdcb3-1873-7e31-a9f3-0e9700e696c7_netLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Issuance of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued_019fdcb3-1873-7204-ad8c-bbc9922724f5_verboseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group, Inc. common stock issued to existing Apollo common stockholders (in shares)</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Equity Interest, Share Issued, Number of Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued"/>
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    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_019fdcb3-19df-784b-8f23-6cffa95e5d6e_terseLabel_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP units</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_label_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP [Member]</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_documentation_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DowlingCapitalPartnersLPMember" xlink:href="skwd-20260930.xsd#skwd_DowlingCapitalPartnersLPMember"/>
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    <link:label id="lab_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_019fdcb3-1977-7127-b1d5-3c3869f7687e_terseLabel_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_label_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense, After Acquisition</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_documentation_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense, After Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:href="skwd-20260930.xsd#skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:to="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_019fdcb3-18ff-72e4-aae7-b3dbfc91eddb_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in receivable/payable for securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_label_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_documentation_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:href="skwd-20260930.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fdcb3-1977-795c-b980-0af241d35581_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fdcb3-1977-7e85-9b31-4bffa2cfbf3d_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Losses and LAE</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
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    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_019fdcb3-1873-7c89-879b-44bf4e251fa7_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancingReceivablePortfolioSegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_019fdcb3-18ff-7965-bf26-c48d0cacadf5_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive securities (in shares)</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
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    <link:label id="lab_us-gaap_NumberOfOperatingSegments_019fdcb3-18ff-7903-a567-4b2b46919071_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of operating segments</link:label>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Operating Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfOperatingSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NumberOfOperatingSegments"/>
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    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_019fdcb3-1900-7543-a191-a214c98cedae_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfGoodwillTextBlock"/>
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    <link:label id="lab_us-gaap_GoodwillGross_label_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillGross"/>
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    <link:label id="lab_dei_EntityCentralIndexKey_019fdcb3-1977-7dfe-be6b-78edf777ea0d_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCentralIndexKey"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCentralIndexKey" xlink:to="lab_dei_EntityCentralIndexKey" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityAbstract_019fdcb3-1977-730f-a4cc-43cb75e23fcc_terseLabel_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_EquityAbstract_label_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityAbstract" xlink:to="lab_us-gaap_EquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year</link:label>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_label_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:to="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_019fdcb3-19df-7c2d-8da0-2a4c7d0a2ac3_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentFixedRatePeriodAxis"/>
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    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_019fdcb3-1977-7008-8fcd-0dcffc08cfe0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:to="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_019fdcb3-18ff-7376-881b-73ee4674cf6d_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DesignatedAsHedgingInstrumentMember_019fdcb3-19df-74c3-96de-b52896cf0b41_terseLabel_en-US" xlink:label="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Designated as Hedging Instrument</link:label>
    <link:label id="lab_us-gaap_DesignatedAsHedgingInstrumentMember_label_en-US" xlink:label="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Designated as Hedging Instrument [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DesignatedAsHedgingInstrumentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:to="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_019fdcb3-1977-7a20-8bfd-9738abfdd8e7_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-For-Sale</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FixedMaturitiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FixedMaturitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FixedMaturitiesMember" xlink:to="lab_us-gaap_FixedMaturitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward_019fdcb3-1977-76f5-b447-01dfd2c51479_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-For-Sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_019fdcb3-18ff-7566-b3ef-6605d15515d9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Components of Income Tax Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Components of Income Tax Expense (Benefit) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_019fdcb3-1978-74b9-923d-49e3d971a762_verboseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Effects of Reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_019fdcb3-19df-797d-a418-18bf34833dde_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, basis spread on variable rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateDomain_019fdcb3-1977-7b08-8b0d-2914cf40c96c_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateDomain" xlink:to="lab_us-gaap_VariableRateDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_019fdcb3-1978-70ed-b68a-9f4a15ee4308_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive loss:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
    <link:label id="lab_ecd_AllIndividualsMember_label_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Individuals [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllIndividualsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllIndividualsMember" xlink:to="lab_ecd_AllIndividualsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_019fdcb3-19df-7922-af90-16b6ee805e24_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale and Held-to-Maturity, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
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    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_019fdcb3-18ff-7415-bf1d-6d228a6291bd_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consideration of Skyward Specialty Insurance Group, Inc. issued common stock</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Equity Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EnergySolutionsMember_019fdcb3-19df-7994-a233-544fc98d1043_terseLabel_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:label id="lab_skwd_EnergySolutionsMember_label_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy Solutions [Member]</link:label>
    <link:label id="lab_skwd_EnergySolutionsMember_documentation_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergySolutionsMember" xlink:href="skwd-20260930.xsd#skwd_EnergySolutionsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergySolutionsMember" xlink:to="lab_skwd_EnergySolutionsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_019fdcb3-18ff-7016-9137-7c8c869021ad_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:label id="lab_us-gaap_StatementLineItems_label_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_019fdcb3-18ff-7347-b35a-28c96899014c_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Assets" xlink:to="lab_us-gaap_Assets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_019fdcb3-19df-76a0-82b9-43914d6c085e_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_019fdcb3-1977-71f8-9f8c-811901cfcb35_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Segments</link:label>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_label_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Segments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingSegmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingSegmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingSegmentsMember" xlink:to="lab_us-gaap_OperatingSegmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SandipKapadiaMember_label_en-US" xlink:label="lab_skwd_SandipKapadiaMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sandip Kapadia [Member]</link:label>
    <link:label id="lab_skwd_SandipKapadiaMember_documentation_en-US" xlink:label="lab_skwd_SandipKapadiaMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Sandip Kapadia</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SandipKapadiaMember" xlink:href="skwd-20260930.xsd#skwd_SandipKapadiaMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SandipKapadiaMember" xlink:to="lab_skwd_SandipKapadiaMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019fdcb3-1977-7a94-973e-8ae6c70a11f2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Gain, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019fdcb3-19df-7440-adf6-c74c6bc7d7e0_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities assumed</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_019fdcb3-18ff-781c-84ef-bbdef7483a18_terseLabel_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment</link:label>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_label_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment [Member]</link:label>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_documentation_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SkywardSpecialtySegmentMember" xlink:href="skwd-20260930.xsd#skwd_SkywardSpecialtySegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SkywardSpecialtySegmentMember" xlink:to="lab_skwd_SkywardSpecialtySegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential_019fdcb3-18ff-7ecf-bead-0ee41971d3ff_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign operations taxed at statutory tax rates</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Foreign Income Tax Rate Differential, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_019fdcb3-1873-7968-8f84-2a42d08a42bd_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoMember_terseLabel_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO</link:label>
    <link:label id="lab_ecd_PeoMember_label_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoMember" xlink:to="lab_ecd_PeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_019fdcb3-19df-7838-bd04-a7c1b31aaffd_terseLabel_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of underwriting divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_label_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_documentation_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfUnderwritingDivisions" xlink:href="skwd-20260930.xsd#skwd_NumberOfUnderwritingDivisions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfUnderwritingDivisions" xlink:to="lab_skwd_NumberOfUnderwritingDivisions" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_019fdcb3-18ff-7224-a11a-f2f19d0bcdbe_terseLabel_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_label_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_documentation_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IntangibleAssetsAcquired" xlink:href="skwd-20260930.xsd#skwd_IntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IntangibleAssetsAcquired" xlink:to="lab_skwd_IntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_019fdcb3-1873-79a6-abe0-155d8905537a_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1971</link:label>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_label_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1971 - Digital Economy [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1971 - Digital Economy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1971DigitalEconomyMember" xlink:href="skwd-20260930.xsd#skwd_Syndicate1971DigitalEconomyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1971DigitalEconomyMember" xlink:to="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_019fdcb3-1977-7a6b-98b8-089b0a0105ee_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Goodwill_019fdcb3-18ff-745c-bf74-b6c6375ce068_netLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Goodwill, net balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_019fdcb3-18ff-7bd9-a865-2f31b213172e_terseLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preliminary allocation to goodwill</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Goodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions_019fdcb3-1977-7745-8186-24c36da331c1_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of securities</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Number of Positions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Accounts Payable, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable"/>
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    <link:label id="lab_us-gaap_RetainedEarningsMember_019fdcb3-18ff-791d-8ed7-02782be727ea_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings:</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_019fdcb3-19df-7ddc-9459-3333cd8dd9d1_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_019fdcb3-18ff-798f-b21c-f9a4982bf1c9_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurements</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementPolicyPolicyTextBlock"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_019fdcb3-1977-75b4-b32f-1d13c6b46853_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019fdcb3-1977-73f4-be9e-1bf6b7d4025a_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019fdcb3-1977-78f2-9599-043ef3e1653f_periodStartLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Common shares balance at beginning of period (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019fdcb3-1977-768e-8484-5b3d4647f61d_periodEndLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Common shares balance at ending of period (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesOutstanding" xlink:to="lab_us-gaap_CommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgDiscLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgDiscLineItems" xlink:to="lab_ecd_AwardTmgDiscLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_019fdcb3-1977-7dd5-8ccf-1ef35dc74265_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_019fdcb3-1978-770e-bad3-d386d8769178_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgencyAgreementMember_019fdcb3-1978-71f3-a33d-31ee51b72c67_terseLabel_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agency agreement</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_label_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Agency Agreement [Member]</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_documentation_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agency Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgencyAgreementMember" xlink:href="skwd-20260930.xsd#skwd_AgencyAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgencyAgreementMember" xlink:to="lab_skwd_AgencyAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward_019fdcb3-18ff-75ee-bb94-b43e10a02b3d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019fdcb3-18ff-7082-8a27-2d064d03f1b7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019fdcb3-18ff-79d7-9404-d499ff5e8788_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization of intangible assets</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:to="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_019fdcb3-1978-74bd-94a8-a268a17bef7a_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Line Items]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_019fdcb3-18ff-7231-b7f8-20023d9d894f_negatedTerseLabel_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LossOnSaleOfOtherInvestments" xlink:href="skwd-20260930.xsd#skwd_LossOnSaleOfOtherInvestments"/>
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    <link:label id="lab_skwd_NumberOfUSSubsidiaries_019fdcb3-19df-7e96-a602-fcacc2d0db62_terseLabel_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of US subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfUSSubsidiaries_label_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of US Subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfUSSubsidiaries_documentation_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of US Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfUSSubsidiaries" xlink:href="skwd-20260930.xsd#skwd_NumberOfUSSubsidiaries"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_019fdcb3-1977-76f5-b4ac-51c338a12051_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenNet_019fdcb3-1977-7b94-85aa-b9fdda945013_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Premiums Written, Net, Total</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:to="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_019fdcb3-1977-72d2-a149-a857679a4583_terseLabel_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_label_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinitelivedIntangibleAssetsAcquired1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:to="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019fdcb3-1977-7f60-bdbf-ca7bb1a2728f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total commission and fee revenue</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer, Excluding Assessed Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_019fdcb3-19df-73cb-8b2c-8f1e6e111571_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Carrying Value of Equity Method Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TrancheADDTLMember_019fdcb3-1978-7d98-aa02-df56219eaf3b_terseLabel_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche A DDTL</link:label>
    <link:label id="lab_skwd_TrancheADDTLMember_label_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tranche A DDTL [Member]</link:label>
    <link:label id="lab_skwd_TrancheADDTLMember_documentation_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tranche A DDTL</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TrancheADDTLMember" xlink:href="skwd-20260930.xsd#skwd_TrancheADDTLMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TrancheADDTLMember" xlink:to="lab_skwd_TrancheADDTLMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_019fdcb3-18ff-70e7-b45f-b7e9533eaef4_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments, Financial Assets, Balance Sheet Groupings [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:to="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingIncomeNet_019fdcb3-1977-7f5f-a4aa-8586bec9c552_totalLabel_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Underwriting income</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_label_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_documentation_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingIncomeNet" xlink:href="skwd-20260930.xsd#skwd_UnderwritingIncomeNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingIncomeNet" xlink:to="lab_skwd_UnderwritingIncomeNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodValue_019fdcb3-19df-710f-9fad-04a18a7188be_terseLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock repurchased during period, value</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodValue_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased During Period, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedDuringPeriodValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedDuringPeriodValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockRepurchasedDuringPeriodValue" xlink:to="lab_us-gaap_StockRepurchasedDuringPeriodValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:to="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019fdcb3-18ff-7074-82ef-b6032d8aa94f_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019fdcb3-1978-71da-8db6-02573a0f8510_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales/Disposals</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Sales</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_019fdcb3-18ff-7c87-8486-4d48766239c8_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_019fdcb3-18ff-764c-ab8f-15a62abd5789_terseLabel_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans receivable</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_label_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_documentation_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansReceivableMeasurementInput" xlink:href="skwd-20260930.xsd#skwd_LoansReceivableMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansReceivableMeasurementInput" xlink:to="lab_skwd_LoansReceivableMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_019fdcb3-1900-7477-95f4-7db95f5e7ff3_terseLabel_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Profit commission &amp; consortium overrider charged to Managed Syndicates</link:label>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_label_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Profit Commission And Consortium Overrider Charged To Managed Syndicates [Member]</link:label>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Profit Commission And Consortium Overrider Charged To Managed Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:href="skwd-20260930.xsd#skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:to="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_019fdcb3-1977-715f-a3f3-c86731d3e87c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCountryMember_019fdcb3-1978-7b85-9b53-fcca758b5ef7_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign</link:label>
    <link:label id="lab_us-gaap_ForeignCountryMember_label_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCountryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCountryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCountryMember" xlink:to="lab_us-gaap_ForeignCountryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_019fdcb3-18ff-7bdf-bee0-303b977339da_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P. [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:href="skwd-20260930.xsd#skwd_BrewerLaneVenturesFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:to="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_019fdcb3-18ff-7238-a04e-d84cfeb56ba7_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_019fdcb3-18ff-7513-b64d-9171252c3895_terseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_label_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Deferred Charges</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfDeferredCharges" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfDeferredCharges"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfDeferredCharges" xlink:to="lab_us-gaap_AmortizationOfDeferredCharges" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_019fdcb3-1977-711a-8ecf-e2ca34316c22_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionDomain" xlink:to="lab_us-gaap_RelatedPartyTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationDisclosureTextBlock_019fdcb3-1977-7776-b56b-5397817743e3_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisitions</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:to="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredCedingCommission_019fdcb3-1977-7b53-85cc-daff12445100_terseLabel_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred ceding commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_label_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredCedingCommission" xlink:href="skwd-20260930.xsd#skwd_DeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredCedingCommission" xlink:to="lab_skwd_DeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_019fdcb3-18ff-7a4e-9c00-ad9c7ad65b91_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non U.S government securities</link:label>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Security, Government, Non-US [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:to="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_019fdcb3-1977-7a29-8ba7-96f7577bd489_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesMember" xlink:to="lab_us-gaap_EquitySecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_019fdcb3-18ff-7301-b3a2-84a46f7d1aa8_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019fdcb3-1900-7d6c-9b58-473703609b8e_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019fdcb3-1978-7fd2-9e07-d9a8cc1ca63b_periodStartLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019fdcb3-1978-78d2-95b8-2297f6717f41_periodEndLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019fdcb3-18ff-7891-a651-6dd05171bfcf_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
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    <link:label id="lab_srt_ProductsAndServicesDomain_019fdcb3-1978-7496-9e21-b877cc87ff36_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_019fdcb3-1977-70aa-808f-3f6ef2387f43_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisaggregationOfRevenueTable"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationProFormaInformationEarningsOrLossOfAcquireeSinceAcquisitionDateActual" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationProFormaInformationEarningsOrLossOfAcquireeSinceAcquisitionDateActual"/>
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    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_019fdcb3-1977-751e-a46c-0b67441a2966_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityLineItems"/>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet_019fdcb3-1977-784e-bff9-ad571d20e1f4_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Liabilities, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxLiabilitiesNet"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate"/>
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    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019fdcb3-1977-706f-9998-0a73c63c892c_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax_019fdcb3-1977-78be-9b20-621592bb5c2e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Foreign currency translation adjustment</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Foreign Currency Translation Adjustment, Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments_01a08633-7881-723c-b8ac-28bc2f862f86_terseLabel_en-US" xlink:label="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total losses for the period recognized in losses and loss adjustment expenses</link:label>
    <link:label id="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments_label_en-US" xlink:label="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement With Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (loss) And Adjustments</link:label>
    <link:label id="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments_documentation_en-US" xlink:label="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement With Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (loss) And Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:href="skwd-20260930.xsd#skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:to="lab_skwd_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossAndAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardGrantDateFairValue_terseLabel_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value as of Grant Date</link:label>
    <link:label id="lab_ecd_AwardGrantDateFairValue_label_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardGrantDateFairValue" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardGrantDateFairValue" xlink:to="lab_ecd_AwardGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_019fdcb3-18ff-7eb1-91e7-ce8c3f15c29d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTableTextBlock" xlink:to="lab_ecd_PvpTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
    <link:label id="lab_ecd_TrdArrDuration_label_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Duration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrDuration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrDuration" xlink:to="lab_ecd_TrdArrDuration" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsAxis_019fdcb3-1873-7f08-b1dd-a14c53cef920_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:label id="lab_srt_ConsolidationItemsAxis_label_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsAxis" xlink:to="lab_srt_ConsolidationItemsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_019fdcb3-1873-7984-8caa-253577b10e00_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressPostalZipCode"/>
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    <link:label id="lab_dei_EntityRegistrantName_019fdcb3-1977-77dc-b404-dc46e9694ae8_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityRegistrantName"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019fdcb3-1977-72d8-8aa4-125b191892b4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_019fdcb3-1977-7447-bb0a-c1cccfefa903_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
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    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:to="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019fdcb3-18ff-79b4-a8a0-7ca079492560_periodStartLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_019fdcb3-18ff-767b-9032-81c97b3c9864_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt"/>
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    <link:label id="lab_skwd_NotesPayableMember_label_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable [Member]</link:label>
    <link:label id="lab_skwd_NotesPayableMember_documentation_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NotesPayableMember" xlink:href="skwd-20260930.xsd#skwd_NotesPayableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NotesPayableMember" xlink:to="lab_skwd_NotesPayableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillRollForward_019fdcb3-18ff-7112-962a-52c441099471_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillRollForward"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019fdcb3-1977-713d-a682-c03a8562c4b1_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
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    <link:label id="lab_us-gaap_TradeNamesMember_019fdcb3-19df-7b15-a314-0ed201d576a7_terseLabel_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trade name</link:label>
    <link:label id="lab_us-gaap_TradeNamesMember_label_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trade Names [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradeNamesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradeNamesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradeNamesMember" xlink:to="lab_us-gaap_TradeNamesMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019fdcb3-18ff-70d8-942f-29390815331b_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
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    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_019fdcb3-18ff-7fa3-93d7-206202d0ab4c_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurements</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_019fdcb3-18ff-718b-a337-81c5f4c4348d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_019fdcb3-1977-7fe0-a7fd-b4f85078f453_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_019fdcb3-1977-79c7-8616-11643e79b4aa_verboseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Estimated Annual Amortization Expense</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths"/>
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    <link:label id="lab_us-gaap_TreasuryStockSharesAcquired_019fdcb3-1873-7150-8b51-c222280f2d29_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockSharesAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Shares acquired (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockSharesAcquired_label_en-US" xlink:label="lab_us-gaap_TreasuryStockSharesAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Shares, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockSharesAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockSharesAcquired"/>
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    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_019fdcb3-18ff-72ad-a6e7-ba6e73d037cc_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2025 [Member]</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2025</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:href="skwd-20260930.xsd#skwd_RevolvingLineOfCreditDueDecember2025Member"/>
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    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_019fdcb3-18ff-7575-977b-715e3c5f1779_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share</link:label>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-1977-7084-95dc-ca71d51886ae_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-1977-72ae-a5d2-4af8a6ee577c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-1977-7929-acdb-fbf5c45f4a49_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
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    <link:label id="lab_us-gaap_OtherAssets_019fdcb3-1873-7c06-bdaf-96b07b67c345_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssets"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockValueAcquiredCostMethod"/>
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    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fdcb3-1977-72d6-b6b6-1bbe931153e8_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents, restricted cash and funds at Lloyd's at beginning of period</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued_019fdcb3-19df-7fdc-8d9a-0e7ed24fc761_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock acquired</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Value, Treasury Stock Reissued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_019fdcb3-19df-7c95-9eac-7750d7fc8448_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:to="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_019fdcb3-1873-7984-9e3c-16ff1d7fba6d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Estimated fair value, indefinite-lived</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Indefinite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_019fdcb3-1978-7bd2-b3e4-6d0903fcf08b_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonNeosMember_terseLabel_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-NEOs</link:label>
    <link:label id="lab_ecd_NonNeosMember_label_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-NEOs [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonNeosMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonNeosMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonNeosMember" xlink:to="lab_ecd_NonNeosMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_019fdcb3-1978-7eea-a012-305adfd752b0_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_label_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses [Text Block]</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_documentation_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:href="skwd-20260930.xsd#skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:to="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_019fdcb3-1978-77bd-94a1-f85e6c08c6f7_terseLabel_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets</link:label>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_label_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets [Member]</link:label>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_documentation_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:href="skwd-20260930.xsd#skwd_CashAndCashEquivalentsAndOtherAssetsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:to="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_019fdcb3-19df-7ce0-99d5-7fab4ddb4def_verboseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Cash consideration</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireBusinessesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019fdcb3-1977-79ac-a5a4-1d32d1f876ee_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership %</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitDomain_019fdcb3-18ff-7c00-ac76-f19228e2ed1f_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitDomain_label_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReportingUnitDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitDomain" xlink:to="lab_us-gaap_ReportingUnitDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_019fdcb3-19df-7962-8bf7-849e05be0135_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_019fdcb3-1900-70fc-9550-218e7adba2db_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_019fdcb3-18ff-74e9-b376-03ee20b8453f_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_019fdcb3-1873-7619-9d77-16541bd5a32d_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
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    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_019fdcb3-1873-7aa4-b2f8-2910c44a69c6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock acquired</link:label>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for Repurchase of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:to="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_019fdcb3-1977-715c-b2c6-c1d3e3b82a81_terseLabel_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP units</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_label_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:href="skwd-20260930.xsd#skwd_ArenaSpecialOpportunitiesFundLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:to="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeAxis_019fdcb3-1977-74bc-8ab6-aa4c8dcc5b76_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_019fdcb3-1873-70a1-bde1-225b09a7abf1_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote</link:label>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_label_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NamedExecutiveOfficersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GlobalAndPropertyMember_019fdcb3-1977-7d85-8c63-a5046ea13e13_terseLabel_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Global Property</link:label>
    <link:label id="lab_skwd_GlobalAndPropertyMember_label_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Global and Property [Member]</link:label>
    <link:label id="lab_skwd_GlobalAndPropertyMember_documentation_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Global and Property</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GlobalAndPropertyMember" xlink:href="skwd-20260930.xsd#skwd_GlobalAndPropertyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GlobalAndPropertyMember" xlink:to="lab_skwd_GlobalAndPropertyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_019fdcb3-1977-7e18-ac13-56139a4e0648_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductOrServiceAxis_019fdcb3-1977-707e-b8cc-f877cb052a9a_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:label id="lab_srt_ProductOrServiceAxis_label_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductOrServiceAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019fdcb3-1900-7a81-a6eb-8d4d71829cfc_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities, at fair value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019fdcb3-1900-772b-8ef7-c22742976339_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_019fdcb3-18ff-76f1-939f-b0794db4e6a6_netLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Common stock:</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_019fdcb3-1978-7249-8a6c-bf7d84b28480_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_019fdcb3-18ff-7cec-9df8-60e5f5f68647_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization, Estimated Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization, Estimated Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_019fdcb3-1977-7468-ae58-9fede4c14e67_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities and stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_019fdcb3-18ff-7009-a2a6-4b6c41556b0b_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:href="skwd-20260930.xsd#skwd_FixedMaturitySecuritiesHeldToMaturityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:to="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019fdcb3-1873-7006-a391-65710e6c9249_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OtherSectorsMember_019fdcb3-18ff-765b-aec7-db06d5ea1b3b_terseLabel_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_label_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Sectors [Member]</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_documentation_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Sectors</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OtherSectorsMember" xlink:href="skwd-20260930.xsd#skwd_OtherSectorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OtherSectorsMember" xlink:to="lab_skwd_OtherSectorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_019fdcb3-19df-79b8-9d95-01da469b847d_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_019fdcb3-1977-7deb-ae47-f3ce67161671_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Purchases</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_019fdcb3-1978-743d-bc89-88531d3f9509_terseLabel_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementBusinessSegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:to="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_label_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Additional402vDisclosureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Additional402vDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_019fdcb3-18ff-757c-abbf-8f8c4d54bfe5_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByAssetClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByAssetClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByAssetClassAxis" xlink:to="lab_us-gaap_FairValueByAssetClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyDomain_019fdcb3-19df-7187-b4bb-7ccc7c49cf02_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related and Nonrelated Parties [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyDomain" xlink:to="lab_us-gaap_RelatedPartyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TabularListTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tabular List, Table</link:label>
    <link:label id="lab_ecd_TabularListTableTextBlock_label_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tabular List [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TabularListTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TabularListTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TabularListTableTextBlock" xlink:to="lab_ecd_TabularListTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_019fdcb3-1977-7f70-8b1b-b074e860e117_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional paid-in capital</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fdcb3-18ff-736c-a0f0-7f5447b21d44_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fdcb3-18ff-746b-bc99-3a5408037f0c_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Plus: reinsurance recoverable on unpaid claims, end of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fdcb3-18ff-7ed0-b759-303f915613b9_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unpaid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_019fdcb3-1978-7290-ab02-269c0762c863_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear_019fdcb3-18ff-7fac-a880-721657c27597_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remainder of 2026</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Remainder of Fiscal Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:to="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditAndSuretyMember_019fdcb3-1977-75e5-856e-f86d87f55b38_verboseLabel_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Credit &amp; Surety</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_019fdcb3-1977-73d6-b18b-17533f1f706f_terseLabel_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit &amp; Surety</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_label_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit And Surety [Member]</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_documentation_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit And Surety</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditAndSuretyMember" xlink:href="skwd-20260930.xsd#skwd_CreditAndSuretyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditAndSuretyMember" xlink:to="lab_skwd_CreditAndSuretyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_label_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:to="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_019fdcb3-1978-7997-bf1d-a06c554d4437_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_019fdcb3-18ff-78e0-9d7d-a6c003926400_terseLabel_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility</link:label>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_label_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility [Member]</link:label>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_documentation_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanCreditFacilityMember" xlink:href="skwd-20260930.xsd#skwd_TermLoanCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanCreditFacilityMember" xlink:to="lab_skwd_TermLoanCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_019fdcb3-18ff-77da-b5b6-86d146219f6b_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Debt Securities, Trading, and Equity Securities, FV-NI</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_019fdcb3-1978-78c7-8ec8-5f68843e24e2_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of securities, allowance for credit loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Number of Positions</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Number of Positions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_019fdcb3-18ff-773f-ad35-43f72b802e95_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash (used in) provided by deposit accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:href="skwd-20260930.xsd#skwd_ProceedsFromPaymentsForDepositAccounting"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:to="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_019fdcb3-1977-7044-998a-901ebfd0b844_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancingReceivablePortfolioSegmentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAxis_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation:</link:label>
    <link:label id="lab_ecd_AdjToCompAxis_label_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToCompAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAxis" xlink:to="lab_ecd_AdjToCompAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:to="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_AggtErrCompAmt_label_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompAmt" xlink:to="lab_ecd_AggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPaidNet_019fdcb3-1977-7b8f-9d04-8b361d3558e3_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash paid for interest</link:label>
    <link:label id="lab_us-gaap_InterestPaidNet_label_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Paid, Excluding Capitalized Interest, Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPaidNet" xlink:to="lab_us-gaap_InterestPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019fdcb3-1977-7aea-a2e4-bd92d91d89ac_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (loss) income:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgingDesignationAxis_019fdcb3-19df-7fbd-9908-49ab156023db_terseLabel_en-US" xlink:label="lab_us-gaap_HedgingDesignationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Designation [Axis]</link:label>
    <link:label id="lab_us-gaap_HedgingDesignationAxis_label_en-US" xlink:label="lab_us-gaap_HedgingDesignationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Designation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgingDesignationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HedgingDesignationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgingDesignationAxis" xlink:to="lab_us-gaap_HedgingDesignationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_019fdcb3-1900-74f8-8e98-d5499009d9bb_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_019fdcb3-1873-741e-8d49-fdbf63254151_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosure" xlink:to="lab_us-gaap_AssetsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GlobalAgricultureMember_019fdcb3-1900-7fea-aa78-dc486bf5dee3_terseLabel_en-US" xlink:label="lab_skwd_GlobalAgricultureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Global Agriculture</link:label>
    <link:label id="lab_skwd_GlobalAgricultureMember_label_en-US" xlink:label="lab_skwd_GlobalAgricultureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Global Agriculture [Member]</link:label>
    <link:label id="lab_skwd_GlobalAgricultureMember_documentation_en-US" xlink:label="lab_skwd_GlobalAgricultureMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Global Agriculture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GlobalAgricultureMember" xlink:href="skwd-20260930.xsd#skwd_GlobalAgricultureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GlobalAgricultureMember" xlink:to="lab_skwd_GlobalAgricultureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureName" xlink:to="lab_ecd_MeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PayVsPerformanceDisclosureLineItems_label_en-US" xlink:label="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PayVsPerformanceDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:to="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_019fdcb3-1977-73eb-9978-faf8c6fe91a1_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_019fdcb3-18ff-760b-9283-58011e48a17a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentLineItems" xlink:to="lab_us-gaap_DebtInstrumentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019fdcb3-18ff-7353-bc7e-ad1294d3f46e_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019fdcb3-18ff-7ba0-9302-f07bb6e3cbf4_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AccidentAndHealthMember_019fdcb3-18ff-7c7c-88e8-bd16b59d442d_terseLabel_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident and Health</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_label_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accident and Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accident and Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentAndHealthMember" xlink:href="skwd-20260930.xsd#skwd_AccidentAndHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentAndHealthMember" xlink:to="lab_skwd_AccidentAndHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_019fdcb3-18ff-72d5-813b-e3235ebd12ba_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional paid-in capital:</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid-in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019fdcb3-1900-72a8-840f-98e3739b3e5e_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndName_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_TrdArrIndName_label_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndName" xlink:to="lab_ecd_TrdArrIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_019fdcb3-1977-79b0-b2ce-e8e1ebd0caf4_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:to="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FHLBLoanMember_019fdcb3-18ff-700b-a35f-eca4a45b3758_terseLabel_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:label id="lab_skwd_FHLBLoanMember_label_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">FHLB Loan [Member]</link:label>
    <link:label id="lab_skwd_FHLBLoanMember_documentation_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FHLBLoanMember" xlink:href="skwd-20260930.xsd#skwd_FHLBLoanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FHLBLoanMember" xlink:to="lab_skwd_FHLBLoanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_019fdcb3-1977-753d-b958-ad1b8cb1edfa_terseLabel_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_label_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Intangible Assets [Roll Forward]</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_documentation_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TotalIntangibleAssetsRollForward" xlink:href="skwd-20260930.xsd#skwd_TotalIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TotalIntangibleAssetsRollForward" xlink:to="lab_skwd_TotalIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_019fdcb3-1977-7bdd-a88e-04a5f381e7b1_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_019fdcb3-18ff-7917-aecf-9a9cd4297f90_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR)</link:label>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_label_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuredOvernightFinancingRateSofrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:to="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_019fdcb3-1977-791c-b935-9b6d0c7ed7fa_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuance of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Shares, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_019fdcb3-18ff-7d16-853c-bc15fd995785_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts and Financing Receivables [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoMember_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO</link:label>
    <link:label id="lab_ecd_NonPeoNeoMember_label_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoMember" xlink:to="lab_ecd_NonPeoNeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings_019fdcb3-1873-74bd-a130-fece58cc552f_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pre-tax gain (loss) adjustment expenses</link:label>
    <link:label id="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings_label_en-US" xlink:label="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Fair Value Hedges Recognized in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:to="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_019fdcb3-18ff-75ae-ae20-a2f498f29d8f_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:href="skwd-20260930.xsd#skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:to="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit_019fdcb3-19df-777a-a1a6-0e9d69e317ea_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income, Operating, Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:to="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMethodTextBlock" xlink:to="lab_ecd_AwardTmgMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019fdcb3-18ff-77b1-8082-9cf189e8e042_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net increase in cash and cash equivalents, restricted cash and funds at Lloyd's</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Period Increase (Decrease), Including Exchange Rate Effect and Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
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    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:to="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_019fdcb3-18ff-7bc8-9944-c31fb866ab9f_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019fdcb3-18ff-70b1-aabb-c376d6504587_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019fdcb3-18ff-7666-b4fb-e86c88d4b05e_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_019fdcb3-18ff-7ba9-8b27-727133b9bd49_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeAxis"/>
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    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis</link:label>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_label_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompAnalysisTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompAnalysisTextBlock"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment_01a19ad3-33da-71c2-a445-29619be74b5d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases (sales) of property and equipment</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfPropertyPlantAndEquipment"/>
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    <link:label id="lab_ecd_RestatementDateAxis_terseLabel_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date:</link:label>
    <link:label id="lab_ecd_RestatementDateAxis_label_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDateAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDateAxis"/>
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    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_019fdcb3-18ff-73cb-a3a3-ac3786293d1d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss)</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract_019fdcb3-18ff-7755-b27d-56fd0d5928ed_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities assumed</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract"/>
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    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_019fdcb3-1977-7332-8a77-fc4cfce4364c_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Funds Held Under Reinsurance Agreements, Liability</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Funds Held Under Reinsurance Agreements, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability"/>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_019fdcb3-1977-7d80-b4a8-d932aaf578af_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations, Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_019fdcb3-1978-70ec-bf21-079776613b59_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans, at fair value</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_019fdcb3-1978-7bf0-a51c-6b7136e5cc9b_verboseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total mortgage loans</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_label_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans on Real Estate, Commercial and Consumer, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:to="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_019fdcb3-1978-702c-93fd-3b19ac5d1b6a_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnBnftsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:to="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_019fdcb3-1977-7dbc-b403-0a7e55ba3408_terseLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_019fdcb3-1977-7be2-8c56-73084e10f9ea_totalLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_label_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_documentation_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:href="skwd-20260930.xsd#skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:to="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019fdcb3-18ff-7f7f-8308-0f55e31e11ea_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Intangible Asset and Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_019fdcb3-18ff-775c-b916-3a7cf27c320c_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_019fdcb3-1873-7037-b112-6b2f9d64ca81_negatedLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalYearFocus_019fdcb3-1873-7f53-97ea-66ddc3b84b67_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalYearFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalYearFocus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentFiscalYearFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalYearFocus" xlink:to="lab_dei_DocumentFiscalYearFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts_019fdcb3-19df-761c-8891-b1810969e7f7_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material transaction expenses</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquisition-Related Cost, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationAcquisitionRelatedCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:to="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_019fdcb3-18ff-76c3-be06-0d8ba5e341ad_terseLabel_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agency fees from syndicates (in percent)</link:label>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_label_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing Agency Fee Percentage</link:label>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_documentation_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing Agency Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingAgencyFeePercentage" xlink:href="skwd-20260930.xsd#skwd_ManagingAgencyFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingAgencyFeePercentage" xlink:to="lab_skwd_ManagingAgencyFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_019fdcb3-18ff-7547-8f90-9383df82eb69_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, $0.01 par value, 500,000,000 shares authorized, 44,846,532 shares issued and 44,413,449 shares outstanding at September&#160;30, 2026; 40,511,222 shares issued and outstanding at December&#160;31, 2025</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockValue" xlink:to="lab_us-gaap_CommonStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_019fdcb3-1977-71a2-aac1-ed41adab8cf0_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_label_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Expense, Operating and Nonoperating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpense" xlink:to="lab_us-gaap_InterestExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_019fdcb3-1977-7c7f-9915-6fbf287382e2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery_019fdcb3-19df-7886-b7b9-4f6951f9624e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, Allowance for Credit Loss, Recovery</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditMember_019fdcb3-19df-73a5-b2b9-1f40fb86e7bb_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditMember" xlink:to="lab_us-gaap_LineOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NonCompetesMember_019fdcb3-18ff-70b9-ae2f-5561b7b89c01_terseLabel_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-competes</link:label>
    <link:label id="lab_skwd_NonCompetesMember_label_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Competes [Member]</link:label>
    <link:label id="lab_skwd_NonCompetesMember_documentation_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Non-Competes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NonCompetesMember" xlink:href="skwd-20260930.xsd#skwd_NonCompetesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NonCompetesMember" xlink:to="lab_skwd_NonCompetesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDeterminationDate_terseLabel_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:label id="lab_ecd_RestatementDeterminationDate_label_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDeterminationDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDeterminationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDeterminationDate" xlink:to="lab_ecd_RestatementDeterminationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AmendmentFlag_019fdcb3-19df-78d9-808f-0e2e4c79715b_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:label id="lab_dei_AmendmentFlag_label_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_AmendmentFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AmendmentFlag" xlink:to="lab_dei_AmendmentFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019fdcb3-18ff-7b0c-88d3-c66096679084_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019fdcb3-18ff-73d9-9e75-43f2276a7e1f_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019fdcb3-18ff-7f91-8629-c99e961438a3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Loss, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_019fdcb3-1977-7058-855d-75a54bded7a8_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rate, First 8 Years</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentFixedInterestRatePeriodOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_019fdcb3-1978-73aa-9115-2e9d2c477c56_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentLosses_019fdcb3-18ff-7605-8886-8bf3970379cf_negatedTotalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_label_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentLosses" xlink:href="skwd-20260930.xsd#skwd_RealizedInvestmentLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentLosses" xlink:to="lab_skwd_RealizedInvestmentLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalHomeLoanBankAdvancesMember_019fdcb3-1977-7e6f-8724-ce8cdb7d4ced_terseLabel_en-US" xlink:label="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Federal Home Loan Bank Advances</link:label>
    <link:label id="lab_us-gaap_FederalHomeLoanBankAdvancesMember_label_en-US" xlink:label="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal Home Loan Bank Advances [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FederalHomeLoanBankAdvancesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:to="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_019fdcb3-1900-7fed-835f-bb075715edeb_terseLabel_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited</link:label>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_label_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited [Member]</link:label>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_documentation_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloGroupHoldingsLimitedMember" xlink:href="skwd-20260930.xsd#skwd_ApolloGroupHoldingsLimitedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApolloGroupHoldingsLimitedMember" xlink:to="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:to="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_019fdcb3-1900-7013-8f33-c38d1246de12_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transfers into Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Transfers Into Level 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_019fdcb3-1978-7550-9324-b324b1e4ac22_terseLabel_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds at Lloyd&#8217;s</link:label>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_label_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Assets, Lloyd's Funds Held</link:label>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_documentation_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Restricted Assets, Lloyd's Funds Held</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RestrictedAssetsLloydsFundsHeld" xlink:href="skwd-20260930.xsd#skwd_RestrictedAssetsLloydsFundsHeld"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RestrictedAssetsLloydsFundsHeld" xlink:to="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_019fdcb3-18ff-78e7-ae8e-ba5db98d35dc_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_019fdcb3-18ff-7468-bad7-af0b82585880_terseLabel_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cover holder relationships</link:label>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_label_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover Holder Relationships [Member]</link:label>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_documentation_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Cover Holder Relationships</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CoverHolderRelationshipsMember" xlink:href="skwd-20260930.xsd#skwd_CoverHolderRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CoverHolderRelationshipsMember" xlink:to="lab_skwd_CoverHolderRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_019fdcb3-18ff-7f73-9172-f617d9bdc582_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of equity securities</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:to="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoTotalCompAmt_label_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoTotalCompAmt" xlink:to="lab_ecd_PeoTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019fdcb3-18ff-7462-b7f1-aa2311647cd5_verboseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Basic (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019fdcb3-18ff-73d7-b4d1-4ddeb2b6ebac_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic weighted-average common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommissionsPolicy_019fdcb3-1977-7a51-aa13-5a635bb59330_terseLabel_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and Fee Income and Underwriting Fee Income</link:label>
    <link:label id="lab_us-gaap_CommissionsPolicy_label_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commissions, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommissionsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommissionsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommissionsPolicy" xlink:to="lab_us-gaap_CommissionsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_019fdcb3-18ff-741b-8153-1b4a404051b7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impaired, Accumulated Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillImpairedAccumulatedImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_019fdcb3-1978-7f22-8448-9e225740a9b9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepositContractsAssets_019fdcb3-1977-7e4e-b004-626de2064380_verboseLabel_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Deposit contracts, assets</link:label>
    <link:label id="lab_us-gaap_DepositContractsAssets_label_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deposit Contracts, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepositContractsAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepositContractsAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepositContractsAssets" xlink:to="lab_us-gaap_DepositContractsAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_019fdcb3-1977-7149-baf4-2045a5562b31_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock_019fdcb3-19df-77fa-b210-579e1b5f9140_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Available-for-Sale, Changes in Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsAbstract_019fdcb3-1977-7375-b7ac-a142e32651a0_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments:</link:label>
    <link:label id="lab_us-gaap_InvestmentsAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsAbstract" xlink:to="lab_us-gaap_InvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_019fdcb3-1977-75e0-a240-6499c03bda1c_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoninterestIncome_019fdcb3-1978-7a89-bae6-26a3f2baeacf_totalLabel_en-US" xlink:label="lab_us-gaap_NoninterestIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net commission and fee income</link:label>
    <link:label id="lab_us-gaap_NoninterestIncome_label_en-US" xlink:label="lab_us-gaap_NoninterestIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noninterest Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoninterestIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoninterestIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoninterestIncome" xlink:to="lab_us-gaap_NoninterestIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_019fdcb3-1978-7e1a-8b3d-3615c11f4f92_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_019fdcb3-1977-7586-8b9b-a0a5681fe8a0_terseLabel_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans, Notes, Trade and Other Receivables Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:to="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_019fdcb3-1978-7f50-aa63-07d1119cd032_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agreement, ownership interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_label_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_documentation_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyOwnershipInterest" xlink:href="skwd-20260930.xsd#skwd_RelatedPartyOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyOwnershipInterest" xlink:to="lab_skwd_RelatedPartyOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiDiscTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:to="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_019fdcb3-1977-7013-88a3-317bc88df25a_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueHedgeAssetsAtFairValue_019fdcb3-1977-7b4a-ba74-ef6139356576_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options, at fair value</link:label>
    <link:label id="lab_us-gaap_FairValueHedgeAssetsAtFairValue_label_en-US" xlink:label="lab_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hedge Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueHedgeAssetsAtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:to="lab_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_019fdcb3-1977-7523-8d03-9b07109193c7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated amortization</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_019fdcb3-18ff-7455-9487-cf13de2ab6e6_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_019fdcb3-18ff-7a2d-b767-e0cb15a22c45_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Unearned Premiums</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_019fdcb3-1977-7de6-99af-ea303c5b69a2_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Investments [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:to="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockValue_019fdcb3-18ff-7ab2-b11e-661de63539ae_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock, at cost, 433,083 and 0 shares, respectively</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValue_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockValue" xlink:to="lab_us-gaap_TreasuryStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnsecuredDebtMember_019fdcb3-18ff-7db7-adfd-e108edc8d7ba_terseLabel_en-US" xlink:label="lab_us-gaap_UnsecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unsecured Debt</link:label>
    <link:label id="lab_us-gaap_UnsecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_UnsecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnsecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnsecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnsecuredDebtMember" xlink:to="lab_us-gaap_UnsecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_019fdcb3-1873-7658-866c-e718f4de19de_terseLabel_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_label_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital [Member]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:href="skwd-20260930.xsd#skwd_MeasurementInputIncrementalCostOfCapitalMember"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019fdcb3-18ff-7c55-8472-19a4c1fb364d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible assets, excluding goodwill, net</link:label>
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    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_019fdcb3-18ff-762f-aa8f-97cc6a652e45_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Security Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAggregatedInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:to="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_019fdcb3-18ff-75e5-aff1-b8661f9472ee_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019fdcb3-1873-7ac4-83a3-be9d68ce5835_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_019fdcb3-18ff-73bc-ad98-4c86636d25ff_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash used in investing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in the Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:to="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_019fdcb3-18ff-7dc5-97b0-29543f9e979b_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders' Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityNoteDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:to="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_019fdcb3-1873-77b8-96b7-db21f027501d_terseLabel_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expenses:</link:label>
    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Costs and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostsAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostsAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostsAndExpensesAbstract" xlink:to="lab_us-gaap_CostsAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_019fdcb3-1977-702c-93d2-46155c637439_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fdcb3-18ff-77b9-a3fb-c5218b2676e0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_019fdcb3-19df-71b1-a835-114a1348bbcf_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total gross written premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019fdcb3-1977-71c9-9082-e25aa280607a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryIndName" xlink:to="lab_ecd_OutstandingRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019fdcb3-18ff-7669-b677-51d166c374af_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale and Maturity of Marketable Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
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    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019fdcb3-1977-7ce4-8775-0cfb24d83736_periodStartLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019fdcb3-1977-70ca-900c-6c95ef7750bf_periodEndLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, Indefinite-Lived</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:to="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsPrrSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:to="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_019fdcb3-1977-7896-bc38-09d0a0205707_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value</link:label>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_label_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Fixed Maturity Securities, Available-for-sale, at fair value</link:label>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Fixed Maturity Securities, Available-For-Sale, At Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:to="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_019fdcb3-18ff-79eb-8255-c929963a82d1_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Denominator</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted, Adjustment [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_019fdcb3-1977-768a-bd50-c9b6b64838a9_totalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019fdcb3-19df-712a-bd7e-38566bd1e0fe_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_019fdcb3-19df-7008-acfe-4d2b48dec4cb_terseLabel_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Miscellaneous fee income</link:label>
    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_label_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Miscellaneous Fee Income [Member]</link:label>
    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_documentation_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Miscellaneous Fee Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MiscellaneousFeeIncomeMember" xlink:href="skwd-20260930.xsd#skwd_MiscellaneousFeeIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MiscellaneousFeeIncomeMember" xlink:to="lab_skwd_MiscellaneousFeeIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019fdcb3-1873-7b55-9b77-5776bfed6a8a_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt, gross</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_019fdcb3-18ff-754b-ab95-62bf527ffa63_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain"/>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionsAbstract_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:to="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryCompAmt" xlink:to="lab_ecd_OutstandingRecoveryCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_IndividualAxis_terseLabel_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Individual:</link:label>
    <link:label id="lab_ecd_IndividualAxis_label_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_IndividualAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_IndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_IndividualAxis" xlink:to="lab_ecd_IndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired_019fdcb3-1977-74bf-88c6-c79f7078a96e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, voting equity interest acquired, percentage</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:to="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019fdcb3-18ff-7050-878b-fc353c368392_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019fdcb3-18ff-77fe-b02d-a90c5703c5dd_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted weighted-average common share equivalents (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_019fdcb3-1977-7ea9-a704-ba35c43cf04b_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisaggregationOfRevenueLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:to="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_019fdcb3-1977-7e20-83aa-1ebbe3e0221c_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, unfunded commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:href="skwd-20260930.xsd#skwd_EquityMethodInvestmentsUnfundedCommitment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:to="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_019fdcb3-18ff-75da-9ed0-b5d19791ff56_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_label_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsNotesAndLoansReceivableLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:to="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_019fdcb3-18ff-7d83-8b78-c8d3b33b1c40_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_019fdcb3-1977-7818-a125-234d3e1ae89f_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:to="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_019fdcb3-18ff-7929-855c-0920d8c4f545_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans in foreclosure</link:label>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_label_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans in Process of Foreclosure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageLoansInProcessOfForeclosureAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:to="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_019fdcb3-1977-70bc-b4d3-1d85c2bb2f26_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Ceded Credit Risk</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:to="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_label_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_019fdcb3-1977-74c7-949a-1c06d5d22c01_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from long term borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_label_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Lines of Credit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromLinesOfCredit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:to="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019fdcb3-1978-7b2d-9930-45811e147764_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_019fdcb3-1978-7655-9db1-a0eb58e5f703_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss"/>
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    <link:label id="lab_us-gaap_MortgageReceivablesMember_019fdcb3-1977-7f01-b7fd-2de0ad67ecb9_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_MortgageReceivablesMember_label_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Receivable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageReceivablesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageReceivablesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageReceivablesMember" xlink:to="lab_us-gaap_MortgageReceivablesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerAbstract_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMFundsLLCMember_019fdcb3-19df-7d06-93f6-9e80cb45b5a5_terseLabel_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_label_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">JVM Funds LLC [Member]</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_documentation_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMFundsLLCMember" xlink:href="skwd-20260930.xsd#skwd_JVMFundsLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JVMFundsLLCMember" xlink:to="lab_skwd_JVMFundsLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockCommonMember_019fdcb3-18ff-752a-9938-4ac947ccc7e6_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock:</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Common [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockCommonMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockCommonMember" xlink:to="lab_us-gaap_TreasuryStockCommonMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_019fdcb3-19df-710e-a033-8225758b6ebe_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:to="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019fdcb3-18ff-78aa-be23-3286b380fdc5_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
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    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_019fdcb3-1977-7fc4-8503-7626eb860283_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative assets, notional amount</link:label>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_label_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Notional Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeAssetNotionalAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:to="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfessionalLinesMember_019fdcb3-18ff-72bd-8c2b-9ff45beb70a4_terseLabel_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Professional Lines</link:label>
    <link:label id="lab_skwd_ProfessionalLinesMember_label_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Professional Lines [Member]</link:label>
    <link:label id="lab_skwd_ProfessionalLinesMember_documentation_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Professional Lines</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfessionalLinesMember" xlink:href="skwd-20260930.xsd#skwd_ProfessionalLinesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfessionalLinesMember" xlink:to="lab_skwd_ProfessionalLinesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_terseLabel_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Executive Categories</link:label>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_label_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Executive Categories [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllExecutiveCategoriesMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllExecutiveCategoriesMember"/>
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    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_019fdcb3-1978-71a2-85af-80bde74de851_terseLabel_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">U.S. government securities</link:label>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">US Government Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_USGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsSvcCstMember" xlink:to="lab_ecd_PnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019fdcb3-1900-710e-8122-92aa0736f197_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
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    <link:label id="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_019fdcb3-1977-70ee-a7bd-f43008d39fec_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
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    <link:label id="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_documentation_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments, After Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:href="skwd-20260930.xsd#skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:to="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements_019fdcb3-18ff-7294-81b9-93ab2d692bdb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Settlements</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Settlements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_019fdcb3-18ff-71a2-9d7d-2b726f2b4c45_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock"/>
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    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureAbstract" xlink:to="lab_us-gaap_DebtDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_019fdcb3-1977-7126-bcb4-024fa99a6fd3_terseLabel_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans not producing income</link:label>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_label_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of Mortgage Loans Not Producing Income</link:label>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_documentation_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of Mortgage Loans Not Producing Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:href="skwd-20260930.xsd#skwd_NumberOfMortgageLoansNotProducingIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:to="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019fdcb3-1977-7ef1-9db7-2ad8d34c4ce8_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables, net</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019fdcb3-1977-7831-a626-a4c9d54ba2c5_totalLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Paid and Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_019fdcb3-18ff-70b2-abbf-0d440a1558a6_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments</link:label>
    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:to="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_019fdcb3-18ff-730c-a723-06d8632e3909_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Maturities, Prepayments and Calls of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
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    <link:label id="lab_srt_MinimumMember_019fdcb3-1977-7e46-a7ea-0443a635bf93_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Low</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_019fdcb3-1977-78f7-bc18-6015d5fe8f23_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeAxis" xlink:to="lab_us-gaap_InvestmentTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_019fdcb3-19df-7e99-a49e-ac878fe3cadc_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue"/>
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    <link:label id="lab_skwd_EnergyMember_019fdcb3-18ff-74a7-bac9-c202562b3739_terseLabel_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:label id="lab_skwd_EnergyMember_label_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy [Member]</link:label>
    <link:label id="lab_skwd_EnergyMember_documentation_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Energy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergyMember" xlink:href="skwd-20260930.xsd#skwd_EnergyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergyMember" xlink:to="lab_skwd_EnergyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_019fdcb3-18ff-7f4b-899b-d1e7c74ba39e_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments, fair value disclosure</link:label>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:to="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_019fdcb3-18ff-7457-9154-46257c12f50e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable"/>
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    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_019fdcb3-1873-7808-89ff-8e80047a5e07_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Revenue</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisaggregationOfRevenueTableTextBlock"/>
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    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_019fdcb3-1978-7655-8f5f-0f48dbf9e1b5_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity Disclosure [Text Block]</link:label>
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    <link:label id="lab_us-gaap_LiabilitiesAbstract_019fdcb3-18ff-7b02-aeb0-c6f971c41a59_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_BusinessAcquisitionLineItems_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionLineItems"/>
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    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesAuthorized"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetUsefulLife"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
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    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardExrcPrice" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardExrcPrice"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_019fdcb3-18ff-7d07-9549-6794e7f686cd_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $4,228 and $468, respectively)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
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    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_019fdcb3-1873-72a0-93ed-3be961d58b4d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
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    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_019fdcb3-18ff-756a-a76a-626b39e69457_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_label_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingInformationLineItems"/>
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    <link:label id="lab_srt_StockRepurchaseProgramAuthorizedAmount1_019fdcb3-19df-7cff-8508-714d99305476_terseLabel_en-US" xlink:label="lab_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share repurchase program, authorized, amount</link:label>
    <link:label id="lab_srt_StockRepurchaseProgramAuthorizedAmount1_label_en-US" xlink:label="lab_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share Repurchase Program, Authorized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StockRepurchaseProgramAuthorizedAmount1"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_019fdcb3-1977-7737-ae36-ad45a50c2796_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, gross unrealized losses</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract"/>
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    <link:label id="lab_dei_DocumentQuarterlyReport_019fdcb3-1977-7db9-a6fd-591666596009_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
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    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_019fdcb3-18ff-7279-8bd8-2861382fef7d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019fdcb3-18ff-715b-a693-18ad5841613a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Payments on long term borrowings</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019fdcb3-18ff-7f0a-af2f-e4b873937ba3_verboseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Repayments of long-term debt</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019fdcb3-1900-7eb3-a0e0-92fe65ff72d5_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019fdcb3-1900-77f6-9e5b-c043f18f1320_netLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019fdcb3-1900-7182-91ad-a85c4dc13b92_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recorded investment balance</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestments" xlink:to="lab_us-gaap_EquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_019fdcb3-18ff-7542-b2db-b83d1cde34ef_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_019fdcb3-1977-7fa4-8e6d-e072de29ee3a_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred policy acquisition costs and VOBA</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_019fdcb3-18ff-7ead-ba2c-b385961333bb_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables, net</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Reinsurance Recoverable, Net</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Reinsurance Recoverable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019fdcb3-19df-724d-8bd9-1fd7e21e8fe4_verboseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total (losses) gains for the period recognized in net investment gains</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_019fdcb3-1873-7f73-9ff1-d19cbb6165cb_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_019fdcb3-18ff-71b4-95be-20b4acd2209d_terseLabel_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LoansReceivableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:to="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfSubsidiaries_019fdcb3-19df-78d9-8341-05cf2086d8c9_terseLabel_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfSubsidiaries_label_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of Subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfSubsidiaries_documentation_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfSubsidiaries" xlink:href="skwd-20260930.xsd#skwd_NumberOfSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfSubsidiaries" xlink:to="lab_skwd_NumberOfSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrAdoptionDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_019fdcb3-1977-7329-85fe-c461a8e3fd09_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_label_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:to="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
    <link:label id="lab_ecd_TrdArrIndTitle_label_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Title</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndTitle" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_019fdcb3-18ff-77b7-84ec-31f7a7385367_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountingPoliciesAbstract_label_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountingPoliciesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountingPoliciesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountingPoliciesAbstract" xlink:to="lab_us-gaap_AccountingPoliciesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_019fdcb3-18ff-7841-b0aa-cdd655210da4_verboseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_019fdcb3-18ff-74a6-b654-b94dff38f185_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:type="arc" order="1"/>
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    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_019fdcb3-1977-7c01-a0b4-e3f20b1cc69f_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commercial</link:label>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_label_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial Portfolio Segment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommercialPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:to="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_019fdcb3-1977-7a30-901c-20135fe9749e_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability For Claims And Claims Adjustment Expense</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability For Claims And Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossLineItems_019fdcb3-1978-7050-880a-c7154fe5ac54_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Line Items]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossLineItems_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsGainLossLineItems"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019fdcb3-1977-7705-9433-74a9e5365768_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_019fdcb3-1900-7462-be94-6d25763b6d27_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, fair value</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_019fdcb3-1977-7153-b484-c9efb5ab181b_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAcquireeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:to="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_019fdcb3-1977-74c2-9ef4-4dc6886cb386_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
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    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
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    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_019fdcb3-18ff-7c11-9f7d-44e9dbdff4bf_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:href="skwd-20260930.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
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    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_019fdcb3-18ff-758d-a420-97060a20ffab_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share</link:label>
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    <link:label id="lab_skwd_ApolloSegmentMember_019fdcb3-18ff-7dc4-9529-87af28af972a_terseLabel_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Apollo Segment</link:label>
    <link:label id="lab_skwd_ApolloSegmentMember_label_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo Segment [Member]</link:label>
    <link:label id="lab_skwd_ApolloSegmentMember_documentation_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloSegmentMember" xlink:href="skwd-20260930.xsd#skwd_ApolloSegmentMember"/>
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    <link:label id="lab_srt_WeightedAverageMember_019fdcb3-18ff-7475-a8aa-1b666b6d417a_terseLabel_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted average</link:label>
    <link:label id="lab_srt_WeightedAverageMember_label_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_WeightedAverageMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_WeightedAverageMember"/>
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    <link:label id="lab_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_019fdcb3-1977-7cc5-a1ad-888321e2f64d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAxis"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fdcb3-1978-7ced-be45-dae6dd12fb6d_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by operating activities</link:label>
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    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_019fdcb3-1900-73e9-bc78-46a8d4a9cdc2_terseLabel_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hospitality</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HospitalityPortfolioSegmentMember" xlink:href="skwd-20260930.xsd#skwd_HospitalityPortfolioSegmentMember"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_019fdcb3-18ff-7b34-a140-7be0c52f0bc2_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019fdcb3-1977-79af-a879-41660e6038ec_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019fdcb3-1977-7f33-bf5f-105596d101a3_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019fdcb3-1977-7ce8-949d-e9f5fbab8002_verboseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_019fdcb3-1977-7339-a8a0-cdfc29e84f98_totalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansMember_019fdcb3-1977-7c2f-8c5f-862aee062c06_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_label_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans [Member]</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_documentation_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansMember" xlink:href="skwd-20260930.xsd#skwd_MortgageLoansMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansMember" xlink:to="lab_skwd_MortgageLoansMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_019fdcb3-1977-77a9-9c56-64f7d84c4a58_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax assets</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:to="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_terseLabel_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs)</link:label>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_label_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockAppreciationRightsSARSMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:to="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_019fdcb3-18ff-7474-b417-bb09e41131b5_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:href="skwd-20260930.xsd#skwd_BrewerLaneVentureFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:to="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_019fdcb3-19df-7cf7-a6fa-e77831821783_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryIndName" xlink:to="lab_ecd_ForgoneRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description</link:label>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_label_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:to="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems_019fdcb3-1977-7ca8-b66a-128fa279e153_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_019fdcb3-1977-781c-bf31-309f7c3aaf13_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in unrealized (losses) gains on investments, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_019fdcb3-18ff-7d47-85c3-0649c70bbcf3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in short-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForProceedsFromShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:to="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TransactionalESMember_019fdcb3-18ff-712c-8815-ee147442a1fc_terseLabel_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S</link:label>
    <link:label id="lab_skwd_TransactionalESMember_label_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S [Member]</link:label>
    <link:label id="lab_skwd_TransactionalESMember_documentation_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TransactionalESMember" xlink:href="skwd-20260930.xsd#skwd_TransactionalESMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TransactionalESMember" xlink:to="lab_skwd_TransactionalESMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_019fdcb3-1977-76b9-b684-555339c3543e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:to="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA1Member_019fdcb3-1978-763c-b58a-50027ccab9d8_terseLabel_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SMA1</link:label>
    <link:label id="lab_skwd_SMA1Member_label_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SMA1 [Member]</link:label>
    <link:label id="lab_skwd_SMA1Member_documentation_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SMA1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA1Member" xlink:href="skwd-20260930.xsd#skwd_SMA1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA1Member" xlink:to="lab_skwd_SMA1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_019fdcb3-1978-78c2-9977-06e221e08d16_verboseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, variable rate</link:label>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_label_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Credit Spread Adjustment</link:label>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentCreditSpreadAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:to="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentGains_019fdcb3-18ff-7dbc-ba5d-5679dacac392_totalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_label_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentGains" xlink:href="skwd-20260930.xsd#skwd_RealizedInvestmentGains"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentGains" xlink:to="lab_skwd_RealizedInvestmentGains" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_019fdcb3-1977-766b-b36b-44418d0139c4_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_label_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:to="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_019fdcb3-18ff-7a11-92aa-b048357d6339_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitAxis_019fdcb3-1977-76cb-841e-3337ac06fe89_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitAxis_label_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReportingUnitAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitAxis" xlink:to="lab_us-gaap_ReportingUnitAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Investments_019fdcb3-18ff-7da8-870d-202b39ce332c_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_019fdcb3-1978-77c1-95a1-35a732bef1e4_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in less than one year</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_019fdcb3-18ff-76e5-8d28-8c218768f1b0_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_label_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_documentation_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:href="skwd-20260930.xsd#skwd_GrossInvestmentIncomeExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:to="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019fdcb3-19df-7ad7-a1b3-505e5bfaf507_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompRecoveryTable_terseLabel_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery</link:label>
    <link:label id="lab_ecd_ErrCompRecoveryTable_label_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompRecoveryTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompRecoveryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompRecoveryTable" xlink:to="lab_ecd_ErrCompRecoveryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019fdcb3-19df-7c56-8af6-decd2d8f3ab8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value Measurement Inputs and Valuation Techniques</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019fdcb3-1977-7f9c-870f-8e3b7fb2db97_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingExpense_019fdcb3-18ff-7996-bbd8-56144b9ef6b5_totalLabel_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting expenses</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_label_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_documentation_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingExpense" xlink:href="skwd-20260930.xsd#skwd_UnderwritingExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingExpense" xlink:to="lab_skwd_UnderwritingExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_019fdcb3-18ff-7a3e-8d62-c0a9495a282a_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCurrentReportingStatus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCurrentReportingStatus" xlink:to="lab_dei_EntityCurrentReportingStatus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_019fdcb3-1873-7453-a59f-e25e1c39c3a0_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnAmt" xlink:to="lab_ecd_TotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JohnBurkhartMember_label_en-US" xlink:label="lab_skwd_JohnBurkhartMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">John Burkhart [Member]</link:label>
    <link:label id="lab_skwd_JohnBurkhartMember_documentation_en-US" xlink:label="lab_skwd_JohnBurkhartMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">John Burkhart</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JohnBurkhartMember" xlink:href="skwd-20260930.xsd#skwd_JohnBurkhartMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JohnBurkhartMember" xlink:to="lab_skwd_JohnBurkhartMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_019fdcb3-1977-701a-acf2-b0843d50484c_terseLabel_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_label_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net [Member]</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_documentation_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SubordinatedDebtNetMember" xlink:href="skwd-20260930.xsd#skwd_SubordinatedDebtNetMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SubordinatedDebtNetMember" xlink:to="lab_skwd_SubordinatedDebtNetMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock_019fdcb3-1978-722e-abc9-db7243b1c62f_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value of Consideration Transferred</link:label>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss_019fdcb3-1873-7bf6-9196-a40c7096cf6c_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortized cost</link:label>
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    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period Two</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_019fdcb3-1978-7c02-b2e2-d86356b58ec0_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from financing activities:</link:label>
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    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_019fdcb3-1977-7802-90af-872ad3af62db_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, unused capacity, commitment fee percentage</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Unused Capacity, Commitment Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage"/>
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    <link:label id="lab_us-gaap_SharesIssuedPricePerShare_019fdcb3-18ff-7d43-8373-4ac2bf9f5780_verboseLabel_en-US" xlink:label="lab_us-gaap_SharesIssuedPricePerShare" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group, Inc. closing stock price on December 31, 2025 (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_SharesIssuedPricePerShare_label_en-US" xlink:label="lab_us-gaap_SharesIssuedPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Price Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharesIssuedPricePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SharesIssuedPricePerShare"/>
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    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019fdcb3-1873-75f3-bb5f-560f10f832f7_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
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    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019fdcb3-19df-7555-a5cb-119f2eea6c50_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_label_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019fdcb3-1977-7d84-a9bb-bfb7c5cdf00a_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019fdcb3-1977-719f-9b75-70fafefb978d_verboseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidReinsurancePremiums"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery_019fdcb3-1900-7619-a0e9-53449f6710d0_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery"/>
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    <link:label id="lab_us-gaap_OtherIncome_019fdcb3-1977-7ef3-bcee-994183506ea6_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other income (loss)</link:label>
    <link:label id="lab_us-gaap_OtherIncome_019fdcb3-1977-7a2d-9d3a-1048b59b7656_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIncome"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019fdcb3-18ff-75e3-8a58-5b61d0c5dca7_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
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    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_019fdcb3-18ff-725f-801d-35f9514ae144_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
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    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_019fdcb3-1900-7b0b-8739-d6335fd665a1_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer [Text Block]</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Allowance for Credit Loss, Writeoff</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019fdcb3-1977-7456-ab48-e3a8364cea6b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_019fdcb3-18ff-7704-81ba-4c952dc0a089_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual_019fdcb3-19df-72b2-a9f3-cd8a2f327f5a_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenue since acquisition date</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquiree's Revenue since Acquisition Date, Actual</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual"/>
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    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
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    <link:label id="lab_ecd_AllTradingArrangementsMember_terseLabel_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Trading Arrangements</link:label>
    <link:label id="lab_ecd_AllTradingArrangementsMember_label_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Trading Arrangements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllTradingArrangementsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllTradingArrangementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllTradingArrangementsMember" xlink:to="lab_ecd_AllTradingArrangementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_019fdcb3-18ff-7357-8498-7666df07ebda_terseLabel_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Partner Syndicates</link:label>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_label_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Platform Partner Syndicates [Member]</link:label>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Platform Partner Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PlatformPartnerSyndicatesMember" xlink:href="skwd-20260930.xsd#skwd_PlatformPartnerSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PlatformPartnerSyndicatesMember" xlink:to="lab_skwd_PlatformPartnerSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019fdcb3-1977-7a36-b6db-6d2253ff7ef3_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_label_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OtherPerfMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OtherPerfMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OtherPerfMeasureAmt" xlink:to="lab_ecd_OtherPerfMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_019fdcb3-1977-7974-85a9-191a611ec262_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:href="skwd-20260930.xsd#skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock"/>
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    <link:label id="lab_dei_CurrentFiscalYearEndDate_019fdcb3-1977-761c-ba8b-26a31e43dd16_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CurrentFiscalYearEndDate"/>
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    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_019fdcb3-1873-7ad1-9f21-4acf9d0087a7_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments and cash</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-term Investments And Cash [Member]</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short-term Investments And Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:href="skwd-20260930.xsd#skwd_ShortTermInvestmentsAndCashMember"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_019fdcb3-1977-7786-af84-a072f0f86965_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="skwd-20260930.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodShares_019fdcb3-19df-7d1d-9dba-a4da417838a0_terseLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock repurchased during period (in shares)</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodShares_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased During Period, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedDuringPeriodShares" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedDuringPeriodShares"/>
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    <link:label id="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount_019fdcb3-18ff-7e38-855d-5fa64dea827b_terseLabel_en-US" xlink:label="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrecorded unconditional purchase obligation</link:label>
    <link:label id="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount_label_en-US" xlink:label="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrecorded Unconditional Purchase Obligation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:to="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year</link:label>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:to="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_019fdcb3-1977-7575-9c8c-7ccfad4e82f4_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_019fdcb3-1977-782b-87ca-0656b17a5933_verboseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Share-based compensation</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Value, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_019fdcb3-1977-7492-a018-9afbde2890c9_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Investments Classified by Contractual Maturity Date</link:label>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019fdcb3-18ff-74b3-b5f7-76575e95c747_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MarkHaushillMember_label_en-US" xlink:label="lab_skwd_MarkHaushillMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mark Haushill [Member]</link:label>
    <link:label id="lab_skwd_MarkHaushillMember_documentation_en-US" xlink:label="lab_skwd_MarkHaushillMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mark Haushill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MarkHaushillMember" xlink:href="skwd-20260930.xsd#skwd_MarkHaushillMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MarkHaushillMember" xlink:to="lab_skwd_MarkHaushillMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RecoveryOfErrCompDisclosureLineItems_label_en-US" xlink:label="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Recovery of Erroneously Awarded Compensation Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:to="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureAxis" xlink:to="lab_ecd_MeasureAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_019fdcb3-1977-78d0-aaef-61ee4fae6194_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Other</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock_019fdcb3-1977-7376-bc2d-0ca9301f9a63_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Assets And Liabilities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Variable Interest Entities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019fdcb3-19df-72f6-83d5-6bc004d1d221_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019fdcb3-19df-7dbc-9092-50c70362796a_periodStartLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Treasury Shares balance at beginning of period (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019fdcb3-19df-7d78-a288-bf5180403b98_periodEndLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Shares balance at Ending of period (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_label_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Common, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonShares" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockCommonShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockCommonShares" xlink:to="lab_us-gaap_TreasuryStockCommonShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019fdcb3-18ff-7ab4-b862-6d2f137719ff_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019fdcb3-18ff-7b7a-85cd-a36555a76a92_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net, Total</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019fdcb3-18ff-7140-866e-001bca235f88_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SpecialtyProgramsMember_019fdcb3-1977-7494-ace7-9e50079a431f_terseLabel_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">strategic distribution partners</link:label>
    <link:label id="lab_skwd_SpecialtyProgramsMember_label_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Specialty Programs [Member]</link:label>
    <link:label id="lab_skwd_SpecialtyProgramsMember_documentation_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Specialty Programs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SpecialtyProgramsMember" xlink:href="skwd-20260930.xsd#skwd_SpecialtyProgramsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SpecialtyProgramsMember" xlink:to="lab_skwd_SpecialtyProgramsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_019fdcb3-18ff-7ad0-ac4f-b93166857a28_terseLabel_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other operating and general expenses</link:label>
    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_label_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Cost and Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherCostAndExpenseOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherCostAndExpenseOperating" xlink:to="lab_us-gaap_OtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_019fdcb3-1977-7835-81ac-b3b9272a3073_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income to net cash provided by operating activities</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_019fdcb3-1977-7c06-8760-2edc6fc75e29_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019fdcb3-18ff-7295-bc88-51e8864ebcef_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyMember_019fdcb3-1900-7893-84e5-8ae6a6ffdb7a_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party</link:label>
    <link:label id="lab_us-gaap_RelatedPartyMember_label_en-US" xlink:label="lab_us-gaap_RelatedPartyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyMember" xlink:to="lab_us-gaap_RelatedPartyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_019fdcb3-19df-793e-b4e5-a2286a632be5_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash paid for income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_label_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Paid, after Refund Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxesPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxesPaidNet" xlink:to="lab_us-gaap_IncomeTaxesPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_019fdcb3-1977-7b23-ab14-8448f7086ad0_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_019fdcb3-1977-7a52-9a60-391914b5fe8b_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateAxis_019fdcb3-1873-7946-aa57-97f417d2dd45_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateAxis" xlink:to="lab_us-gaap_VariableRateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_019fdcb3-18ff-7f77-a0dc-dcc738d06da9_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_019fdcb3-1900-7d5b-9427-76e609b706b1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Reclassification adjustment for gains on securities no longer held, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Reclassification Adjustment from AOCI for Sale of Securities, Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntitySmallBusiness_019fdcb3-18ff-79ed-be30-5e9d20ae5a16_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_019fdcb3-18ff-72e8-962e-28747d4c954e_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnearnedPremiums_019fdcb3-1873-79af-baa2-5adf855d0ffa_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApolloMember_019fdcb3-1977-7e70-a0c3-6a5fc920e81c_verboseLabel_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Apollo</link:label>
    <link:label id="lab_skwd_ApolloMember_label_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo [Member]</link:label>
    <link:label id="lab_skwd_ApolloMember_documentation_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloMember" xlink:href="skwd-20260930.xsd#skwd_ApolloMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApolloMember" xlink:to="lab_skwd_ApolloMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019fdcb3-1873-7090-ba37-ee8a58f8ef65_terseLabel_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Estimated average useful life (in years)</link:label>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_label_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired, Weighted-Average Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:to="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_019fdcb3-1977-72b6-a369-02b9f4ec89fc_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, interest rate floor</link:label>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_label_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate Floor</link:label>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate Floor</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentInterestRateFloor" xlink:href="skwd-20260930.xsd#skwd_DebtInstrumentInterestRateFloor"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentInterestRateFloor" xlink:to="lab_skwd_DebtInstrumentInterestRateFloor" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable_019fdcb3-1873-712b-907a-08fdc85b22cd_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Table]</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_019fdcb3-1977-75d9-aaea-d454f0c42c8a_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_terseLabel_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value</link:label>
    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_label_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MnpiDiscTimedForCompValFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:to="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_019fdcb3-18ff-7eef-b3ba-d2e65358e876_terseLabel_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Managing agency fees</link:label>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_label_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing Agents Fees [Member]</link:label>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_documentation_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing Agents Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingAgentsFeesMember" xlink:href="skwd-20260930.xsd#skwd_ManagingAgentsFeesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingAgentsFeesMember" xlink:to="lab_skwd_ManagingAgentsFeesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_019fdcb3-19df-7102-8e27-e82ddbf56f02_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying equity</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Underlying Equity in Net Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:to="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_019fdcb3-1977-762c-bbe2-dd72ceef0b10_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SUA commission revenue</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:href="skwd-20260930.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentType_019fdcb3-18ff-7b06-add0-f0f9cba8e462_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
    <link:label id="lab_dei_DocumentType_label_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentType"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentType" xlink:to="lab_dei_DocumentType" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissions_019fdcb3-1978-7abc-a8f3-740ff68e1403_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commissions</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissions_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissions" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissions" xlink:to="lab_us-gaap_InsuranceCommissions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_019fdcb3-1978-7c6f-bb23-7216c9863362_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Acquisitions, net of cash acquired</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Net of Cash Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
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    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_019fdcb3-18ff-76bd-b308-efa85e241c7c_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Summary of Significant Accounting Policies</link:label>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Significant Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SignificantAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-18ff-7fb5-a7be-f5bb52b60dfb_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-18ff-7756-95e0-b2be1c2cd1f3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-18ff-7c22-9d03-64c780c52ff8_periodStartLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019fdcb3-18ff-79fb-9b5c-52e80af1be20_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019fdcb3-1977-7951-aa2d-1f79178df43d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from long term borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_019fdcb3-18ff-70e7-8614-b15fbf575824_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in direct and indirect loans</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:href="skwd-20260930.xsd#skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:to="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_019fdcb3-1977-7d6f-8a8f-86178b456898_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_019fdcb3-1977-7fa6-be4e-84bfc6469c73_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherShortTermInvestments" xlink:to="lab_us-gaap_OtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fdcb3-1977-7284-b492-a0554bed2fda_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fdcb3-1977-7bfc-91de-7057dd583b56_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
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    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_019fdcb3-18ff-7ed6-a88d-f4b8c1f12d84_terseLabel_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_label_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Other Investments</link:label>
    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_documentation_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnrealizedGainLossOnOtherInvestments" xlink:href="skwd-20260930.xsd#skwd_UnrealizedGainLossOnOtherInvestments"/>
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    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_019fdcb3-18ff-7f27-af0d-a67353028aa5_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:to="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_label_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent_01a18d53-852b-7006-8f43-f1cfdbdb0d24_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock based compensation percent</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_019fdcb3-18ff-7d27-92ec-11507f1c60aa_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_019fdcb3-1900-70e3-a3a6-6bb2f4a45415_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsRollForward"/>
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    <link:label id="lab_skwd_TermLoanFacilityMember_019fdcb3-1977-75ec-a40e-3a3efebe969f_terseLabel_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Term Loan Facility, net of debt issuance costs</link:label>
    <link:label id="lab_skwd_TermLoanFacilityMember_label_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Facility [Member]</link:label>
    <link:label id="lab_skwd_TermLoanFacilityMember_documentation_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanFacilityMember" xlink:href="skwd-20260930.xsd#skwd_TermLoanFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanFacilityMember" xlink:to="lab_skwd_TermLoanFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_terseLabel_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Executive Category:</link:label>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_label_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Executive Category [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ExecutiveCategoryAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ExecutiveCategoryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ExecutiveCategoryAxis" xlink:to="lab_ecd_ExecutiveCategoryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CounterpartyNameAxis_019fdcb3-18ff-727a-92aa-54842aacdd28_terseLabel_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:label id="lab_srt_CounterpartyNameAxis_label_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CounterpartyNameAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CounterpartyNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CounterpartyNameAxis" xlink:to="lab_srt_CounterpartyNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_019fdcb3-18ff-7d72-9925-0167fbccdba8_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities and stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_019fdcb3-1977-7c82-a5a9-b9c0bdd041e3_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Market value of trust funds</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_019fdcb3-18ff-7061-8c99-464f4f3afc7d_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgCompActuallyPaidAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:to="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_019fdcb3-18ff-7212-bae4-e9979c69a47a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_019fdcb3-18ff-743f-a125-371671b68a8a_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental disclosure of cash flow information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShakoorKhanMember_label_en-US" xlink:label="lab_skwd_ShakoorKhanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shakoor Khan [Member]</link:label>
    <link:label id="lab_skwd_ShakoorKhanMember_documentation_en-US" xlink:label="lab_skwd_ShakoorKhanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Shakoor Khan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShakoorKhanMember" xlink:href="skwd-20260930.xsd#skwd_ShakoorKhanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShakoorKhanMember" xlink:to="lab_skwd_ShakoorKhanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_019fdcb3-18ff-7a59-a759-9898f2a552c7_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoName" xlink:to="lab_ecd_PeoName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019fdcb3-18ff-75b1-b2dc-d7fc1e1510b0_totalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total paid</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_019fdcb3-1977-71eb-b9f7-e36e83e770f8_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_country_BM_019fdcb3-1873-7c24-a0d0-8abd227e3c2e_terseLabel_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:label id="lab_country_BM_label_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_BM" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_BM"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_BM" xlink:to="lab_country_BM" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_019fdcb3-19df-7833-a42a-c7afc3930355_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_StockUnitsMember_019fdcb3-18ff-7cf0-8e3f-186e5bdac5ed_terseLabel_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock units</link:label>
    <link:label id="lab_skwd_StockUnitsMember_label_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Units [Member]</link:label>
    <link:label id="lab_skwd_StockUnitsMember_documentation_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stock Units</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StockUnitsMember" xlink:href="skwd-20260930.xsd#skwd_StockUnitsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_StockUnitsMember" xlink:to="lab_skwd_StockUnitsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract_019fdcb3-1977-7786-aa3b-386066ba98d0_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Asset [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_019fdcb3-1978-7c6d-ba5d-69a1a5ac01ce_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenGrossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:to="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayable_019fdcb3-1977-73c4-a8b3-a6c8753172b9_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_us-gaap_NotesPayable_label_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NotesPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesPayable" xlink:to="lab_us-gaap_NotesPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock_019fdcb3-1978-7a81-b68e-08ff372df014_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Identifiable Intangible Assets</link:label>
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    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_019fdcb3-18ff-7c67-88de-9be1994c7aec_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized losses</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Losses [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:href="skwd-20260930.xsd#skwd_GrossRealizedInvestmentLossesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_019fdcb3-1977-71dc-bc6f-d1a2dc7b1f58_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded paid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables on Paid Losses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLossesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_019fdcb3-18ff-7267-9404-c49cc83dc93c_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BaseRateMember_019fdcb3-1977-7f3f-9095-46e9581b2779_terseLabel_en-US" xlink:label="lab_us-gaap_BaseRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Base Rate</link:label>
    <link:label id="lab_us-gaap_BaseRateMember_label_en-US" xlink:label="lab_us-gaap_BaseRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Base Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BaseRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BaseRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BaseRateMember" xlink:to="lab_us-gaap_BaseRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined</link:label>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_label_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompNotYetDeterminedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:to="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_terseLabel_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement</link:label>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_label_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MtrlTermsOfTrdArrTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:to="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year</link:label>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:to="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_019fdcb3-1977-72cb-9c83-f192e09f66bf_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities_019fdcb3-18ff-7d63-9314-6adfa1c43fa8_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls and paydowns of fixed maturity securities held-to-maturity</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Maturities, Prepayments and Calls of Held-to-Maturity Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:to="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_019fdcb3-1977-7328-a3f0-8dddc962512a_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_019fdcb3-18ff-7dce-9e26-b97e453a5b8c_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingArrLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingArrLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingArrLineItems" xlink:to="lab_ecd_InsiderTradingArrLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_019fdcb3-1977-7a9a-9c0a-ab15a04f7c44_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales of and distributions from equity method and other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForProceedsFromLongtermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:to="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_019fdcb3-1873-79b4-aad3-c42b71686abd_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember"/>
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    <link:label id="lab_skwd_RISCOMMember_019fdcb3-1977-7d00-9981-ab8e4b640922_terseLabel_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">RISCOM</link:label>
    <link:label id="lab_skwd_RISCOMMember_label_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">RISCOM [Member]</link:label>
    <link:label id="lab_skwd_RISCOMMember_documentation_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">RISCOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RISCOMMember" xlink:href="skwd-20260930.xsd#skwd_RISCOMMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RISCOMMember" xlink:to="lab_skwd_RISCOMMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_019fdcb3-1977-7f2e-b361-aa122c633f29_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosureItemAmountsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:to="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription_019fdcb3-1978-7d13-a6c2-bae41519a5f5_terseLabel_en-US" xlink:label="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reclassifications</link:label>
    <link:label id="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription_label_en-US" xlink:label="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reclassification, Comparability Adjustment [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PriorPeriodReclassificationAdjustmentDescription"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:to="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_country_GB_019fdcb3-18ff-71a0-9967-ca615fde128f_terseLabel_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">UK</link:label>
    <link:label id="lab_country_GB_label_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED KINGDOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_GB" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_GB"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_GB" xlink:to="lab_country_GB" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_019fdcb3-1977-73c0-9683-543e41c14cb3_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_019fdcb3-18ff-7afc-b0ce-1a2c26ddbbf8_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans uncollectable write-off</link:label>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_label_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans Uncollectable Write-Off</link:label>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_documentation_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans Uncollectable Write-Off</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansUncollectableWriteOff" xlink:href="skwd-20260930.xsd#skwd_MortgageLoansUncollectableWriteOff"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansUncollectableWriteOff" xlink:to="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsMember" xlink:to="lab_ecd_EqtyAwrdsAdjsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_019fdcb3-1977-7418-b87c-16c56da535f2_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgingRelationshipDomain_019fdcb3-18ff-7bf3-8661-e8519c7e53fa_terseLabel_en-US" xlink:label="lab_us-gaap_HedgingRelationshipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Domain]</link:label>
    <link:label id="lab_us-gaap_HedgingRelationshipDomain_label_en-US" xlink:label="lab_us-gaap_HedgingRelationshipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgingRelationshipDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HedgingRelationshipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgingRelationshipDomain" xlink:to="lab_us-gaap_HedgingRelationshipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_019fdcb3-1977-7034-ab8c-2db8a9c60df7_terseLabel_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans held-for-investment, term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_label_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_documentation_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansHeldForInvestmentTerm" xlink:href="skwd-20260930.xsd#skwd_LoansHeldForInvestmentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansHeldForInvestmentTerm" xlink:to="lab_skwd_LoansHeldForInvestmentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedPremium_019fdcb3-19df-7a5b-8e97-7609f6bfa0a0_terseLabel_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total managed premiums</link:label>
    <link:label id="lab_skwd_ManagedPremium_label_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managed Premium</link:label>
    <link:label id="lab_skwd_ManagedPremium_documentation_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managed Premium Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagedPremium" xlink:href="skwd-20260930.xsd#skwd_ManagedPremium"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagedPremium" xlink:to="lab_skwd_ManagedPremium" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_019fdcb3-18ff-7553-b1c1-c686e7f1e39a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_019fdcb3-1977-7104-acd7-40f49a7d067a_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:to="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_019fdcb3-18ff-7fe7-9b49-7d725d2e0246_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and Loss Adjustment Expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:to="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_019fdcb3-18ff-7880-93de-57150b5a253d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_019fdcb3-19df-78a6-b512-19452e63c884_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held-to-maturity, fair value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract"/>
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    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_019fdcb3-1977-7623-ac92-90de16ffd4cd_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate expenses</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_019fdcb3-18ff-7dfb-923a-42fdf230e4ef_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_label_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_documentation_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansUnrealizedGainLoss" xlink:href="skwd-20260930.xsd#skwd_MortgageLoansUnrealizedGainLoss"/>
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    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_019fdcb3-18ff-7274-a5bc-de5a3b4a9fbe_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commercial mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
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    <link:label id="lab_us-gaap_HedgingDesignationDomain_019fdcb3-1978-7cbf-9957-04a2c6b272b9_terseLabel_en-US" xlink:label="lab_us-gaap_HedgingDesignationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Designation [Domain]</link:label>
    <link:label id="lab_us-gaap_HedgingDesignationDomain_label_en-US" xlink:label="lab_us-gaap_HedgingDesignationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Designation [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgingDesignationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HedgingDesignationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgingDesignationDomain" xlink:to="lab_us-gaap_HedgingDesignationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal_019fdcb3-1900-7e70-8f7d-06571ccd99c2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period provision for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_terseLabel_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Available</link:label>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_019fdcb3-1978-737a-9739-49ea4c72a1c3_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:to="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock_019fdcb3-1978-7761-866a-70eb2fc74324_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Held-to-Maturity, Changes in Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_019fdcb3-18ff-7bfa-9532-4dbe8fe958da_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_019fdcb3-18ff-73b0-8bd3-77fd84a200ae_terseLabel_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainOnSaleOfOtherInvestments" xlink:href="skwd-20260930.xsd#skwd_GainOnSaleOfOtherInvestments"/>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_019fdcb3-18ff-710d-a41d-209290dccafc_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_019fdcb3-18ff-71ef-9d70-2ca0d6a100ae_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Ceded Unearned Premium</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Ceded Unearned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium"/>
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    <link:label id="lab_ecd_PvpTable_terseLabel_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure</link:label>
    <link:label id="lab_ecd_PvpTable_label_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTable"/>
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    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_019fdcb3-1977-732b-a79e-efaaf5036e1b_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SUA fee income</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:href="skwd-20260930.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019fdcb3-1873-7ebd-a734-55c992229928_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019fdcb3-1873-7520-b30f-2b4653b52543_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred</link:label>
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    <link:label id="lab_dei_EntityFilerCategory_019fdcb3-1977-785a-87aa-576eb6b37d0e_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFilerCategory"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019fdcb3-18ff-730a-997d-39ba136e4e9a_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position</link:label>
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    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_019fdcb3-19df-7c21-95d0-4345d7afa6fe_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Numerator</link:label>
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    <link:label id="lab_skwd_AgentRelationshipMember_019fdcb3-1900-70d0-b3a9-b09317236509_terseLabel_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agent Relationships</link:label>
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    <link:label id="lab_skwd_AgentRelationshipMember_documentation_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agent Relationship</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipMember" xlink:href="skwd-20260930.xsd#skwd_AgentRelationshipMember"/>
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    <link:label id="lab_skwd_ArenaSOPLPMember_019fdcb3-1978-7ba6-a0be-22afcbd97834_terseLabel_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arena SOP LP units</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_label_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Arena SOP LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Arena SOP LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSOPLPMember" xlink:href="skwd-20260930.xsd#skwd_ArenaSOPLPMember"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
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    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:to="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_019fdcb3-1977-74d7-b6f1-2db5f22ead4d_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:to="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_019fdcb3-1977-773f-87e9-abea04cc2ba7_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Gain (Loss) on Securities</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:to="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss_019fdcb3-1977-752d-84ca-47cfaf955b46_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total gains (losses) for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Asset, Recurring Basis, Still Held, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SyndicateMember_019fdcb3-1977-7020-811e-802de0981df3_terseLabel_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate Capacity</link:label>
    <link:label id="lab_skwd_SyndicateMember_label_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate [Member]</link:label>
    <link:label id="lab_skwd_SyndicateMember_documentation_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SyndicateMember" xlink:href="skwd-20260930.xsd#skwd_SyndicateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SyndicateMember" xlink:to="lab_skwd_SyndicateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_019fdcb3-19df-7e6e-b6f9-94dd838f00a7_terseLabel_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Abstract]</link:label>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_label_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Abstract]</link:label>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_documentation_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Variable Interest Entity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_VariableInterestEntityAbstract" xlink:href="skwd-20260930.xsd#skwd_VariableInterestEntityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_VariableInterestEntityAbstract" xlink:to="lab_skwd_VariableInterestEntityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine2_019fdcb3-18ff-7b2e-9919-1b1a645e0090_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine2_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressAddressLine2"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine2" xlink:to="lab_dei_EntityAddressAddressLine2" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_019fdcb3-1977-79fb-9b13-cb35c106e33e_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred policy acquisition costs and VOBA</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Deferred Policy Acquisition Costs and VOBA</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Deferred Policy Acquisition Costs and VOBA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:href="skwd-20260930.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock_019fdcb3-1977-7874-9d63-da8a9b69cdeb_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign Currency</link:label>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Foreign Currency Transactions and Translations Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:to="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_019fdcb3-18ff-71d1-9a70-dfc9cee9fd19_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine1_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_019fdcb3-1873-744c-8843-a95af3e89f25_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total expenses</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Benefits, Losses and Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses" xlink:to="lab_us-gaap_BenefitsLossesAndExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_019fdcb3-18ff-7545-92c1-cfa7391284a4_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueHedgingMember_019fdcb3-1977-7ff4-9d5b-ec70728a96d2_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueHedgingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hedging</link:label>
    <link:label id="lab_us-gaap_FairValueHedgingMember_label_en-US" xlink:label="lab_us-gaap_FairValueHedgingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hedging [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueHedgingMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueHedgingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueHedgingMember" xlink:to="lab_us-gaap_FairValueHedgingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_019fdcb3-1977-7119-a779-422e7fa16452_terseLabel_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_label_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Due August 2029 [Member]</link:label>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_documentation_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Due August 2029</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanDueAugust2029Member" xlink:href="skwd-20260930.xsd#skwd_TermLoanDueAugust2029Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanDueAugust2029Member" xlink:to="lab_skwd_TermLoanDueAugust2029Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_019fdcb3-1977-7f4f-adb8-3433bcee316d_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums and commissions receivable, net</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember_019fdcb3-1977-7a01-bc8d-5d34a34c5d81_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityPrimaryBeneficiaryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:to="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_019fdcb3-19df-73bf-9c2b-0bc92f4aeafd_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Deferred Tax Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_019fdcb3-1977-7812-8042-1245d0beaacd_totalLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total incurred, net of reinsurance</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_label_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_documentation_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:href="skwd-20260930.xsd#skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:to="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_019fdcb3-1977-7a35-a835-4caf478cbe5e_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:label id="lab_us-gaap_StatementTable_label_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementTable" xlink:to="lab_us-gaap_StatementTable" xlink:type="arc" order="1"/>
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