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  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA1</link:label>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_583b21b2-982d-446a-ae2f-e26af7deb24e_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred income taxes</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_3175ec24-75da-4f21-9132-77cc9629cc0d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_b97bbba4-a526-4a39-8d62-3d4508f7e1f5_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable including reinsurance premium paid</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableMember" xlink:to="lab_us-gaap_ReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_296f6b06-9a88-4320-8190-74228d548a25_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_e7806ad5-513f-495b-859a-950f4efbc8f9_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted, weighted average exercise price (in usd per share)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Excluding Shares Issued in Connection with Acquisition, Weighted Average Exercise Price</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:to="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_a7144eae-686d-43f1-b892-3614a0570fb9_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue"/>
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    <link:label id="lab_skwd_RestrictedStockAwardsAndUnitsMember_902c9006-68c7-4255-92be-de04af7f88c0_terseLabel_en-US" xlink:label="lab_skwd_RestrictedStockAwardsAndUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Stock Awards And Units</link:label>
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    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_b725242e-331b-4094-a249-83a23d0f84dd_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_ebfb86f3-2227-4649-b634-8d1d1f575105_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_450cd6a3-ac15-43dc-b2ba-9ee2b9732c15_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred shares, if converted</link:label>
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    <link:label id="lab_srt_RangeMember_3e3cf3a1-841e-4486-883a-fe657d038b39_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/srt-2022.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_StockIssuedDuringPeriodSharesStockOptionsExercised_32f7af3e-cd46-41c6-aaaf-041c20879b8c_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercised (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised"/>
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    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_43d86e60-e37a-4213-b8cf-794ce907e817_verboseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indirect loans</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_32505800-62ba-4f0e-89da-9de6ad872e69_terseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in indirect loans and loan collateral</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indirect Loans and Loan Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:href="skwd-20230331.xsd#skwd_IndirectLoansAndLoanCollateralMember"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_2925353d-f83a-4ece-93e3-a9cc1ebf1369_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales and maturities of investment securities</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
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    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_30c5bf7b-8d84-48c4-bf8b-91d482110d6b_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unsecured subordinated notes</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unsecured Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:href="skwd-20230331.xsd#skwd_UnsecuredSubordinatedNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:to="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_821422f5-7c06-481f-a3e0-267cf8613c0c_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock conversion to common shares</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Issued During Period, Value, Conversion of Convertible Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_38008c24-b663-4969-9cbb-ce4e1e9c3d2f_terseLabel_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office</link:label>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OfficePortfolioSegmentMember" xlink:href="skwd-20230331.xsd#skwd_OfficePortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OfficePortfolioSegmentMember" xlink:to="lab_skwd_OfficePortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_6ae643a8-73bf-4b29-baac-adc58075312b_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance agreement</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_label_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Agreement [Member]</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_documentation_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceAgreementMember" xlink:href="skwd-20230331.xsd#skwd_ReinsuranceAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceAgreementMember" xlink:to="lab_skwd_ReinsuranceAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_5198cb18-ae96-4ec0-a07f-67a6b180e71c_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_48452e22-f865-4d1f-a686-b7d70de86147_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_MeasurementInputTypeDomain_36501cf2-87ec-430a-a294-322ad5fe881a_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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"/>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_5bb5247f-1444-418e-9b35-f5fcdec3204a_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAxis_44a00086-7bbc-4c0d-aa64-16213bb51694_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CumulativeEffectPeriodOfAdoptionAxis"/>
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    <link:label id="lab_us-gaap_RelatedPartyDomain_8783c28d-56aa-465c-94d6-eb29612c56fc_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party [Domain]</link:label>
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    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_54d89f05-7263-4a7a-b8d4-b1f61028cd44_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_5dc437b7-3918-4a54-895c-e48dbdc6cbec_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available-for-sale and held-to-maturity, fair value</link:label>
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    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_d891bcd8-baf5-487d-bd51-18965a9190ce_terseLabel_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans</link:label>
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    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_53db7b33-5570-44db-9796-ff12681c9515_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SUA fee income</link:label>
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    <link:label id="lab_us-gaap_Liabilities_36b3938a-4b28-4acf-93a6-536e41067ab3_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities</link:label>
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    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_a3a1f8e7-d75a-4544-a89b-4fa96b819359_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Domain]</link:label>
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    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_5325af6b-b143-4d67-a8d6-1f188d0952a9_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
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    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_0498ede8-8af9-421c-ba87-77f4d5ff9bff_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving credit facility</link:label>
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    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_dcccdfef-5f77-45d1-b9c9-341ab8dfb0c0_terseLabel_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial</link:label>
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    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_15aea2e5-bdcf-4b79-9aa6-63ee1dd483d3_terseLabel_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hospitality</link:label>
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    <link:label id="lab_skwd_LongTermIncentivePlanMember_357ecf49-ec1c-4601-9712-fe7407a8b1ac_terseLabel_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Incentive Plan</link:label>
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    <link:label id="lab_skwd_LongTermIncentivePlanMember_documentation_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Incentive Plan</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_93892c1c-fdb8-4f12-835d-1f48a9e46e2d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available for sale, fair value</link:label>
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    <link:label id="lab_us-gaap_FinancialInstrumentAxis_d2f68c39-0d6d-46ed-94f2-7964c0c53f16_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentAxis" xlink:to="lab_us-gaap_FinancialInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_9619851e-6f85-4771-87bc-ee66439b4377_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total gains for the period recognized in net investment gains (losses)</link:label>
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    <link:label id="lab_srt_AffiliatedEntityMember_f9ecc552-dd5f-410d-b987-52ed5ccbb37c_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Affiliated entity</link:label>
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    <link:label id="lab_skwd_OtherSectorsMember_21c0333d-2e67-4c79-8faa-bbb4d04fbb0e_terseLabel_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
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    <link:label id="lab_dei_DocumentPeriodEndDate_cff2d97e-fe73-4c01-a728-3762011f4663_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Period End Date</link:label>
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    <link:label id="lab_skwd_DeferredCedingCommission_0e37191a-79d4-41d5-bb4f-c403cfce4a8f_terseLabel_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred ceding commission</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_78d5fff1-b3e1-4c95-b738-a32f68f32b96_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
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    <link:label id="lab_skwd_WestaimHIIGLPMember_d809fccc-818c-47c0-9a96-54001f2772e3_terseLabel_en-US" xlink:label="lab_skwd_WestaimHIIGLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_33d5c98d-fb4b-4904-9a04-dd4d28596cde_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss)</link:label>
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    <link:label id="lab_us-gaap_Assets_5b43f6df-c487-45d5-809b-37908fd62a2a_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total assets</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_61b457d7-b4b6-4f32-a669-3cd62658209d_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common shares</link:label>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Payout, Percentage</link:label>
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    <link:label id="lab_us-gaap_PerformanceSharesMember_4873bdbe-e5e7-416e-a738-0f1823c31236_terseLabel_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Performance condition awards</link:label>
    <link:label id="lab_us-gaap_PerformanceSharesMember_label_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Performance Shares [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PerformanceSharesMember" xlink:to="lab_us-gaap_PerformanceSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockLiquidationPreference_103b59b8-5801-4709-bfd2-0e1873bdca50_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockLiquidationPreference" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, liquidation preference (in dollars per share)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockLiquidationPreference" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockLiquidationPreference"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_b8fb7e7e-e8b6-4125-9f4e-cb295d92f89a_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash provided by financing activities</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
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    <link:label id="lab_us-gaap_LongTermDebtFairValue_773d58ec-8d91-4ebf-9e10-3c89da87080a_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtFairValue"/>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
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    <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_us-gaap_LineOfCreditMember_846c998d-c971-4b04-93c2-cc9cde098b8f_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_AssetBackedSecuritiesMember_343aa98f-92ab-4088-befc-7385d8739870_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset-backed securities</link:label>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_c2eef559-fef5-467f-aae7-b5034ab37dfa_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income before income taxes</link:label>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_9e53fb7b-b494-464e-a87b-0789057db681_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Domain]</link:label>
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    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_8bbbe327-56ec-477c-a7ff-992ba16204f3_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans in foreclosure</link:label>
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    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_436d3227-a739-49b3-ac3d-11f7260c5fe2_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_8213a1e7-2773-4119-a636-1dad4c10cba0_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance_286c7935-481f-4bd3-9c39-54374dc0b269_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Write-offs of uncollectible premiums receivable</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss, Writeoff</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:to="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_ce14cac5-996d-4836-9849-247abff167e3_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.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_skwd_LoansReceivableMeasurementInput_6e41db39-ed92-41f7-bc01-e81a979ffd31_terseLabel_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansReceivableMeasurementInput" xlink:href="skwd-20230331.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_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_skwd_LoansHeldForInvestmentTerm_5dc499f7-925f-4ba5-b751-36d46acd491d_terseLabel_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansHeldForInvestmentTerm" xlink:href="skwd-20230331.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_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_0c297c65-d280-4578-be50-4dd901ff5b47_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_cd10ba07-4f2f-4aac-8473-9dbc231d9ee7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_c87b0ebf-7504-43f8-85a5-67a53fc6d3ce_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans (at fair value as of March 31, 2023; at amortized cost as of December 31, 2022)</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_a11c4d13-b32b-4b27-8a50-d8a1219d81da_verboseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_5bf0a089-2152-4859-bd16-6f9cd7a608ce_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_41d234ac-ce31-4a31-8bc6-85ecaf85c456_totalLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.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_dei_EntityAddressCityOrTown_b7b63434-98d6-46dd-840e-ff78f007a623_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/dei-2022.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_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_c3186078-bd01-45ee-8d76-11be4d46147f_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net change in unrealized gains (losses) 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_4a0c1ea2-f57a-4600-8077-cf17c7ee27db_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_MutualFundMember_af32d608-22df-4b01-a9b9-78a25d917714_terseLabel_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mutual funds:</link:label>
    <link:label id="lab_us-gaap_MutualFundMember_label_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mutual Fund [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MutualFundMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MutualFundMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MutualFundMember" xlink:to="lab_us-gaap_MutualFundMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_07fad025-0de6-4a65-850c-3822ae8bd090_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized gains and losses on investments:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Unrealized Gain (Loss) [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesUnrealizedGainLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_1ab586ba-a71f-496f-8a7e-a158d3dea45f_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Receivable for securities sold</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:to="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_f6529239-abb3-4d46-8470-15b62c07e08e_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Axis]</link:label>
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    <link:label id="lab_srt_MinimumMember_3a682b8a-0035-4d4b-97f6-64519e655e58_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Low</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_8d213d56-76a8-4c2c-994f-cf19adb75bd4_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due in less than one year</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
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    <link:label id="lab_dei_EntityEmergingGrowthCompany_96807c51-3b66-4af8-b031-a709c7824a35_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Emerging Growth Company</link:label>
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    <link:label id="lab_srt_CreditRatingAMBestDomain_7332dbc9-f1d9-4775-8b03-6eb43d703a10_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
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    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_527383f7-cfc1-4a82-86bc-e8c07aae9e9c_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, par value (in USD per share)</link:label>
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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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_28573620-4c9e-48cf-a6dc-b104b25335cb_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition costs</link:label>
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    <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_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_0f78be8f-45b3-40b8-8884-c83a17de78dd_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Axis]</link:label>
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    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_c1f95ae8-6cc9-4df0-b2a3-01c14f704189_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums</link:label>
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    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_b083d4b3-48c3-4b4f-980d-2c6da03b891a_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair ValueMeasurements</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_07c8b268-e864-4ecc-9a3f-a549d2a2cc3f_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available for sale, gross unrealized losses</link:label>
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    <link:label id="lab_dei_TradingSymbol_84a39e8b-74bb-4eaf-9800-1cc39fa3ccba_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading Symbol</link:label>
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    <link:label id="lab_dei_EntityFileNumber_00baed20-ead1-4fd8-ad6a-5f66b8b23aca_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
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    <link:label id="lab_skwd_EverestReinsuranceCoMember_f55ac733-4f21-4e8a-94d2-f1ebb369768a_terseLabel_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Everest Reinsurance Co</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_EverestReinsuranceCoMember" xlink:href="skwd-20230331.xsd#skwd_EverestReinsuranceCoMember"/>
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    <link:label id="lab_skwd_AgencyAgreementMember_4e314703-1b42-46c7-8b29-c0d4b3f6a249_terseLabel_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agency agreement</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agency Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgencyAgreementMember" xlink:href="skwd-20230331.xsd#skwd_AgencyAgreementMember"/>
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    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_6078ca4a-d7e3-4851-b4f7-ea2b7ae4f4da_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Draw on revolving line of credit</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_8d6d71b9-5e2e-4acd-bc35-7a8cdeead859_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Taxes</link:label>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_8934b0f7-38ef-408b-b019-88d935ece0c9_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Continuing Operations, Net of Tax, Attributable to Parent</link:label>
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    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_9b0dacb3-22be-4541-9558-96016e9f7d35_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityDomain_d38efb8f-8823-41ff-8021-568dc108f9cd_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Domain]</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_63b1cd6f-2fe5-4db6-af35-866862cd6aaa_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
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    <link:label id="lab_us-gaap_InterestPaidNet_5b46a99b-c0ed-4ba9-9814-2503842a8244_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash paid for interest</link:label>
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    <link:label id="lab_us-gaap_EarningsPerShareBasic_7d2c6ada-1a7b-46fc-bd89-b9992656ccf8_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basic earnings per share (in dollar per share)</link:label>
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    <link:label id="lab_srt_DirectorMember_4b99fa9a-3a39-48a1-a560-06162341de9e_terseLabel_en-US" xlink:label="lab_srt_DirectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Director</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_2504ccf4-9ae7-45f6-9a11-61e2c3579837_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited (in dollars per share)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_e8b5dc13-1455-48bd-8afa-64b6e4e23b66_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from (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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.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_srt_OwnershipDomain_28293fe9-0e12-44e9-afbe-672f16b5db3d_terseLabel_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:label id="lab_srt_OwnershipDomain_label_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_OwnershipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipDomain" xlink:to="lab_srt_OwnershipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_536d05a8-bbce-4cbe-9bbd-4003e87204e6_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/dei-2022.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_CommercialMortgageBackedSecuritiesMember_8a0ee4fa-5850-4b78-ae2a-4f94d262e8b6_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_e231ec02-5b95-4692-91ca-d471c21056d7_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, number of shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock, Number of Shares Issued in Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:to="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_a7a7509b-b76f-4165-aafc-cb7055867dba_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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-20230331.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_us-gaap_CededPremiumsEarned_c8b60468-df6a-48e9-94c7-be7f9cd51582_negatedLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_fea01e5e-1de5-4107-a525-746329766b1c_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_d9087d13-b7d4-46ca-9f73-85a6602ea7c2_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_a5d0dfc4-215c-4905-a373-1897647eef8d_verboseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently issuable instruments (treasury stock method) (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Contingently Issuable Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:to="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_a9b02d01-0583-4c98-a6f4-29ef89849357_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_c5e844ac-4758-4fa9-b6dd-c9dd6f95b11d_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement</link:label>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PortionAtFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsMember_11f542e8-4423-46b2-bada-0cbd766d59db_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Deficit</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_skwd_SMA2Member_867e3484-8196-49c9-a1b0-f8661993944f_terseLabel_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA2Member" xlink:href="skwd-20230331.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_RISCOMMember_04f8b76d-e489-4602-b934-cb5a70e983c1_terseLabel_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RISCOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RISCOMMember" xlink:href="skwd-20230331.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_skwd_BToBMember_3d0cac30-7f08-436a-8912-5981e91f82bb_terseLabel_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">B++ to B+</link:label>
    <link:label id="lab_skwd_BToBMember_label_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">B++ to B+ [Member]</link:label>
    <link:label id="lab_skwd_BToBMember_documentation_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">B++ to B+</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BToBMember" xlink:href="skwd-20230331.xsd#skwd_BToBMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BToBMember" xlink:to="lab_skwd_BToBMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_539b0a97-5d00-463c-b349-2037fd663e87_netLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock</link:label>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_a3370258-0a68-4a11-a3e3-5377ed8ed174_totalLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total other comprehensive income (loss)</link:label>
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    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_4f3cf10a-f512-4ede-bd55-ee9f9d45d626_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Employee equity transactions</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
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    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_f2d19fb0-be32-47cb-ae2d-aac52692574e_terseLabel_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditSpreadAdjustmentMember" xlink:href="skwd-20230331.xsd#skwd_CreditSpreadAdjustmentMember"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_ed746eaf-4c4f-4950-a1fa-88abdfc9cd4c_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20230331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
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    <link:label id="lab_us-gaap_StatementTable_4c4d9604-a1fc-40af-a4fa-db82cc90f5de_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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"/>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_51569b01-4bca-401a-8606-dc1c585fdf2e_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current period change for estimated uncollectible premiums</link:label>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumReceivableCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:to="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_31f93ba9-9c7b-4428-8789-a13f6517ba72_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentQuarterlyReport_78e130ce-bea5-4317-8790-c39fc3923da8_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Quarterly Report</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditLossTable_5a397073-b3b6-419f-b4ec-f9a108aa1e80_terseLabel_en-US" xlink:label="lab_skwd_CreditLossTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Loss [Table]</link:label>
    <link:label id="lab_skwd_CreditLossTable_label_en-US" xlink:label="lab_skwd_CreditLossTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Loss [Table]</link:label>
    <link:label id="lab_skwd_CreditLossTable_documentation_en-US" xlink:label="lab_skwd_CreditLossTable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditLossTable" xlink:href="skwd-20230331.xsd#skwd_CreditLossTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditLossTable" xlink:to="lab_skwd_CreditLossTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LetterOfCreditMember_0f537da8-91c8-49be-a494-a8fd39f4ab28_terseLabel_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Letter of Credit</link:label>
    <link:label id="lab_us-gaap_LetterOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Letter of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LetterOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LetterOfCreditMember" xlink:to="lab_us-gaap_LetterOfCreditMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_MortgageReceivablesMember_f553a4c0-81c4-482b-80cf-92dcfbc2ec0b_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Receivable [Member]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RangeAxis"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_783a0a66-5b5c-4275-a68f-6f7a4e0d09bb_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
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    <link:label id="lab_skwd_TermLoanDueDecember2024Member_0358bc48-7e04-4b9b-8857-d8a22a8b9557_terseLabel_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term loan, due December 31, 2024</link:label>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue_a40e1703-1bfc-4b03-a366-e59b033b8e75_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock options granted to employees</link:label>
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    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_8eb0b33b-148a-4214-9a00-ebc929e83063_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Funds held for others</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_23acd06c-ee89-4c5d-822c-039be27f0de2_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax expense</link:label>
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    <link:label id="lab_us-gaap_CreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_CreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Loss [Abstract]</link:label>
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    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_cbfd626c-6b60-4f09-806d-70c04c11572c_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid-in Capital</link:label>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_73343f42-48f3-40f3-8f68-7dd80db8d9ea_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_1ba8c712-b5fa-4a82-9b6d-1d3d2e09e0dd_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_WeightedAverageNumberOfDilutedSharesOutstanding_ff078182-c878-41a6-bc55-978c57aff345_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Diluted (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_10c47a50-7687-4e64-8c4e-af6426c89246_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
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    <link:label id="lab_skwd_JuniorSubordinatedInterestDebenturesMember_df65d4da-8ca2-46d7-aaf2-d4fbdef3dfc6_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior subordinated interest debentures</link:label>
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    <link:label id="lab_skwd_JuniorSubordinatedInterestDebenturesMember_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Interest Debentures</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:href="skwd-20230331.xsd#skwd_JuniorSubordinatedInterestDebenturesMember"/>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1_5908d233-f2f4-4ecb-9596-bc5e8a12c232_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contractual term</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_1b79c369-c508-47c8-a7e1-941d6a9158d0_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities, at fair value</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_3cfb7f9f-e551-460b-b790-25bd509cb230_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_Investments_4550ada1-c6e0-4c24-8fee-1b685d882380_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_CommonStockValue_0c0c37ac-d6c4-4ba1-a28e-918faa95ec24_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, $0.01 par value, 500,000,000 and 168,000,000 shares authorized, 37,658,111 and 16,832,955 shares issued, respectively</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockValue"/>
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    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_9497809c-9dd1-418c-ab63-319ef59c73a6_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carrying Value</link:label>
    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CarryingReportedAmountFairValueDisclosureMember"/>
    <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"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_4e1ad232-f1f8-4141-9d6e-68996ba667f5_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_8f1a3d03-038f-465e-a5ca-bdc8fee3d298_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Paid losses and loss adjustment expense ceded</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_PreferredStockMember_04f060fd-2a99-4ea5-8859-1c8366f1d58e_netLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_dd76e952-d076-4402-8ba1-0ebf5a8e6913_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stocks:</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_label_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockMember" xlink:to="lab_us-gaap_PreferredStockMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_8a35f82f-9e7e-4b2b-95c1-b729b85c6165_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value (amortized cost of $718,395 and $662,616, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_20488163-2f0f-413e-b326-de905573381b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total fixed maturity securities, available-for-sale</link:label>
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    <link:label id="lab_srt_CounterpartyNameAxis_c8150598-ab95-4e5d-a5d5-ce4b99da7b36_terseLabel_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Axis]</link:label>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward_d8117235-afbc-452f-b984-047798bde3f2_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Roll Forward]</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_cb51d592-ea30-43c1-8a7e-1144e2e8c5ff_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions</link:label>
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    <link:label id="lab_skwd_MarketConditionAwardsMember_cfcaabbf-621e-4de3-9c57-312605b7f2ac_terseLabel_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market condition awards</link:label>
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    <link:label id="lab_skwd_MarketConditionAwardsMember_documentation_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market Condition Awards</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber_227e1a5e-2edc-425a-bf9d-5a3a933ebdf1_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, beginning of period (in shares)</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable_6843dbf2-974e-4576-b119-56e89704b2b5_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Table]</link:label>
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    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_4a4aa02b-520e-4953-9507-d774c296a519_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
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    <link:label id="lab_us-gaap_IPOMember_bb062a96-c565-4250-acc9-e95336ca6a70_terseLabel_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IPO</link:label>
    <link:label id="lab_us-gaap_IPOMember_label_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IPO [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IPOMember" xlink:to="lab_us-gaap_IPOMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_2b1d8aae-e22f-474b-b7a6-721fa2834c21_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
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    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_e51f5864-5b1b-448a-90b5-e203b165d349_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Presentation</link:label>
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    <link:label id="lab_us-gaap_LiabilitiesAbstract_4d0ae672-3a63-488c-98e3-aed2dff2e269_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities [Abstract]</link:label>
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    <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"/>
    <link:label id="lab_skwd_TreasuryStockParValue_a91ecbea-3709-4889-84b1-a1085894188f_terseLabel_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, par value (in USD per share)</link:label>
    <link:label id="lab_skwd_TreasuryStockParValue_label_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Par Value</link:label>
    <link:label id="lab_skwd_TreasuryStockParValue_documentation_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Par Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TreasuryStockParValue" xlink:href="skwd-20230331.xsd#skwd_TreasuryStockParValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TreasuryStockParValue" xlink:to="lab_skwd_TreasuryStockParValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_72e74b26-2660-4123-a41a-7131a5a2a511_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Numerator</link:label>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_label_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock Dividends and Other Adjustments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:to="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_5c36390f-835e-4d7f-8bbf-f81d4bb97bae_periodStartLabel_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_2e525a88-0999-45fd-a5fe-c35576327f22_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative effect of adoption of ASU 2016-13 at January 1, 2023</link:label>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_3f41d41d-076b-437d-99da-2b89d4beae47_periodEndLabel_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_label_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Doubtful Accounts, Premiums and Other Receivables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:to="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_90c8de49-1f8a-4f9f-a9ca-eb06614b120b_terseLabel_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-family</link:label>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-Family Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-Family Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MultiFamilyPortfolioSegmentMember" xlink:href="skwd-20230331.xsd#skwd_MultiFamilyPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MultiFamilyPortfolioSegmentMember" xlink:to="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestAxis_39610f13-e950-46b7-aa4f-280cdb88df36_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestAxis_label_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CreditRatingAMBestAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestAxis" xlink:to="lab_srt_CreditRatingAMBestAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_d600e10d-0259-4292-8d07-408d7fb39310_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Repayment of term loan</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_EmployeeStockOptionMember_7384f81e-a4bc-48c3-bff5-8d5a485bbcde_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Options (treasury stock method)</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_TreasuryStockValue_b22f4076-1bcc-4b83-8eec-221309435733_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, $0.01 par value, 0 and 233,289 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_srt_TitleOfIndividualWithRelationshipToEntityDomain_21f28944-0808-48e1-ad35-7f1ada979dc8_terseLabel_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Domain]</link:label>
    <link:label id="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain_label_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_TitleOfIndividualWithRelationshipToEntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:to="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_6c0a1327-9c7c-4de1-b605-2635afbdd4f0_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving credit facility</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Line Of Credit Due December 2024 [Member]</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Line Of Credit Due December 2024</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:href="skwd-20230331.xsd#skwd_RevolvingLineOfCreditDueDecember2024Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:to="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_a609f368-ba21-4dd9-b489-8996f6f5c3cc_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_5ee9b819-2493-4cfe-b724-1e768f789cac_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:href="skwd-20230331.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_SaleOfStockPricePerShare_eefe3824-6cb1-4ca5-9d12-060bfbd5b2aa_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, price per share (usd per share)</link:label>
    <link:label id="lab_us-gaap_SaleOfStockPricePerShare_label_en-US" xlink:label="lab_us-gaap_SaleOfStockPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock, Price Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockPricePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockPricePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockPricePerShare" xlink:to="lab_us-gaap_SaleOfStockPricePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_d3bdfa68-950e-400a-a3ab-2ccd80e11ac4_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares authorized (in shares)</link:label>
    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_72fd136c-f9eb-4568-83be-07a14835de6c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.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_CommercialPortfolioSegmentMember_c56c2955-77aa-4d3a-ba62-5cb3b97aeb0a_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_srt_MaximumMember_4e00403a-a51a-40a3-ad90-115d94273355_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">High</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_a43f04c5-6289-4d02-992d-941532e97c21_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated other comprehensive loss</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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_5c3da5bb-86b0-4c08-aac6-b85124d296fc_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current period change for estimated uncollectible reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:to="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_028db53b-0c5c-4777-9fcd-9276638e7589_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, at Carrying Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.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_dei_EntitySmallBusiness_d10d63e9-5d01-4dca-9f43-498fe2885054_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/dei-2022.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_FairValueByMeasurementBasisAxis_2ce13ee1-3cbc-4a9c-95fa-b2ff7f563876_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_StockholdersEquityNoteDisclosureTextBlock_47c6d67d-0d8a-43ee-b0d7-716f8a18a247_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Note Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.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_RevenuesAbstract_231716c9-cea1-47bd-9694-4fe1ab4aa080_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_96943f5b-f8c5-4c92-9bf1-092b323dcd4a_terseLabel_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accordion feature, increase limit</link:label>
    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_label_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Accordion Feature, Increase Limit</link:label>
    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_documentation_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of credit facility, accordion feature, increase limit, subject to certain conditions by obtaining additional commitments from existing and/or new lenders.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:href="skwd-20230331.xsd#skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:to="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_db22bb34-5dcf-4cd9-b468-75beecd5c0ea_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of illiquid investments</link:label>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:href="skwd-20230331.xsd#skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:to="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansMember_46a7d74b-9310-407e-824d-e2532f4e4e85_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansMember" xlink:href="skwd-20230331.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_PaymentsToAcquireAvailableForSaleSecuritiesDebt_21d94424-c966-47f4-8644-4a152bdb1336_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_skwd_NotesPayableMember_3cb237f6-7ebf-460a-b84b-b7d516ef185d_terseLabel_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes payable</link:label>
    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NotesPayableMember" xlink:href="skwd-20230331.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_SignificantAccountingPoliciesTextBlock_f1dffa9d-90ef-4d48-9c0a-75de9356afea_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_PremiumsEarnedNet_2a6bf67e-ad17-4d91-8227-9df08f33825a_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_dd49761e-7a1f-48ff-bdaf-1e7908a5b40d_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_b5411fd6-fb18-48ab-b861-0f6dbfcef940_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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_us-gaap_PremiumsWrittenGrossAbstract_c263959d-8a3c-4f92-a829-be907112d245_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.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"/>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_3ac9c1d4-8ac8-49b3-aa8b-71f301b067dc_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total commission and fee income</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentTable_32a39d86-d396-482c-89e4-a6035d7bb2bf_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
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    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_aede142d-be31-405d-a7dc-73beddee9cdb_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Based Compensation</link:label>
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    <link:label id="lab_us-gaap_OtherAssets_9788d9f8-7c76-423e-9b00-a181900a1ef2_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other assets</link:label>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_09024760-8a55-4d7e-96ae-d45f9bb81316_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commission and Fee Income</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_ab1004b2-63b2-4a8f-aeef-47e0428cd2cf_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Amortized Cost</link:label>
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    <link:label id="lab_skwd_ServiceConditionAwardsMember_3cbe7543-6689-4207-a66b-934603010ba8_terseLabel_en-US" xlink:label="lab_skwd_ServiceConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Service condition awards</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_84272c8b-deb9-40ec-91dc-3188b737c7d3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after ten years</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_e7f85b62-2553-425e-9df7-6b4b4d7c8771_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_713e2ffc-9457-42f8-8bee-af4eda58faf1_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, beginning of period, net of reinsurance</link:label>
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    <link:label id="lab_us-gaap_EquitySecuritiesMember_9fff9530-44ec-462f-bf0c-0c566170e506_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
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    <link:label id="lab_skwd_SecuredOvernightFinancingRateSOFRMember_22c7dae4-ff6c-4c54-b84c-cc989c7f2276_terseLabel_en-US" xlink:label="lab_skwd_SecuredOvernightFinancingRateSOFRMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured Overnight Financing Rate (SOFR)</link:label>
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    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_3832f13f-f550-4436-a049-088ccb85bd83_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
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    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_09461f9a-9f2a-4428-96b8-90ef966d9df6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_524c8636-c435-4591-b5bb-03780e784c32_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Period of adoption, adjustment</link:label>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_1a22db8d-976f-4502-98f5-efd6d0c0acee_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain (Loss)</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_e6979364-eebf-4453-b25d-045cbb8e0f61_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_663a58ea-011b-46e7-ab95-141c04ee503d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Change in short-term investments</link:label>
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    <link:label id="lab_dei_EntityAddressAddressLine2_d04c5992-0608-4ee5-89a4-1ec6b285b09b_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line Two</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceTextBlock_56bc2c2d-ebdf-41b4-9873-cf4cdfe763f6_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance [Text Block]</link:label>
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    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_ccd0f065-86cc-4800-9150-c2206055e9b2_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total expenses</link:label>
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    <link:label id="lab_srt_ProductOrServiceAxis_e4ed1ec6-f833-42c6-9015-0f3e24eaccaf_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/srt-2022.xsd#srt_ProductOrServiceAxis"/>
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    <link:label id="lab_us-gaap_OverAllotmentOptionMember_e7524dda-dcb6-404a-a737-84c1d824dc3d_terseLabel_en-US" xlink:label="lab_us-gaap_OverAllotmentOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Over-Allotment Option</link:label>
    <link:label id="lab_us-gaap_OverAllotmentOptionMember_label_en-US" xlink:label="lab_us-gaap_OverAllotmentOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Over-Allotment Option [Member]</link:label>
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    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_2d41e0b7-45ba-4036-9d88-cf455deb8952_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
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    <link:label id="lab_us-gaap_CededPremiumsWritten_bb53714f-a13e-4fa4-a915-c2555d6d41d9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded premiums</link:label>
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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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
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    <link:label id="lab_us-gaap_SubsidiarySaleOfStockLineItems_e142efbf-2434-4819-80d2-58423e431b80_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsidiary, Sale of Stock [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiarySaleOfStockLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsidiarySaleOfStockLineItems"/>
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    <link:label id="lab_us-gaap_InterestExpense_b51ce3e8-3c7a-430d-9458-01e84987edbe_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_32cddb19-d883-4917-b80d-283a9a85b091_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
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    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_5158ba8e-87ab-493d-9233-cd77e2ce6f7f_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss portfolio transfer</link:label>
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    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_308427d9-0af0-4859-a723-90430b6e0597_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investment income</link:label>
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    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_3402f313-1665-44b7-bb85-fed63b5752c1_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and Loss Adjustment Expenses</link:label>
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    <link:label id="lab_skwd_CommoditySectorMember_7a2ec9b1-e556-4488-b502-8a7c9132ecef_terseLabel_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commodity</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock_71d385d0-57d0-465b-9b0f-0bb5487dd02a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Nonvested Share Activity</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_79618d17-b4a2-4f81-9349-cf6689d84100_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized Cost</link:label>
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    <link:label id="lab_skwd_ConsumerStaplesSectorMember_fb4d23e1-5a6b-488b-ad73-63c263a7723d_terseLabel_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer staples</link:label>
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    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_3b99ec34-7c2b-4e47-ae0e-9df7f9e50b36_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
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    <link:label id="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription_2cdcf6da-53a6-4789-b3bf-cdb9c10cd38f_terseLabel_en-US" xlink:label="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Recent Account Standards Adopted and Updates to Significant Accounting Policies</link:label>
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    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_ade25a0f-7820-4556-9c64-f0ae4a94ee00_terseLabel_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Dowling Capital Partners LP units</link:label>
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    <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" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerAbstract"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_a9988880-4af8-45cc-bce2-531acd1d6ff3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" 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" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Equity Securities, FV-NI</link:label>
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    <link:label id="lab_skwd_FixedIncomeSectorMember_3ffbf66a-1d66-44d8-9b8e-6459fdb5b332_terseLabel_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed income</link:label>
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    <link:label id="lab_dei_EntityCentralIndexKey_60354080-c125-4465-a605-052d3e77a263_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Central Index Key</link:label>
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    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_902a028e-ffab-4b38-a24f-aeb8c5a8344f_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_4474d434-19f5-441a-8b2c-a947725a9e09_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-Average Grant-Date Fair Value</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_0700da2f-09d3-4f2e-b5f6-8af348a55547_periodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
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    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_aa249291-6896-47ac-bb04-e6e34c4a195b_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial</link:label>
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    <link:label id="lab_us-gaap_AssetsAbstract_d9ae31b9-dd88-461c-9e5c-5f16ad639507_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
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    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_a303241d-2b2a-4d87-9835-969db31227d7_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
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