<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019c43d6-dc8d-76fd-b037-0562bf177b68,g:c872802f-08a5-495a-9935-51ca91afa922-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:xbrldt="http://xbrl.org/2005/xbrldt" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/all" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#all"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#hypercube-dimension"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#dimension-default"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#dimension-domain"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/domain-member" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#domain-member"/>
  <link:roleRef roleURI="http://skywardinsurance.com/role/Cover" xlink:type="simple" xlink:href="skwd-20260106.xsd#Cover"/>
  <link:definitionLink xlink:role="http://skywardinsurance.com/role/Cover" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentInformationLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationTable_019c43d6-dc8d-70f8-bdff-7259b5476b07" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentInformationTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_DocumentInformationTable_019c43d6-dc8d-70f8-bdff-7259b5476b07" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationDocumentAxis_019c43d6-dc8d-7ef9-8819-0035cb7af7c8" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentInformationDocumentAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_dei_DocumentInformationTable_019c43d6-dc8d-70f8-bdff-7259b5476b07" xlink:to="loc_dei_DocumentInformationDocumentAxis_019c43d6-dc8d-7ef9-8819-0035cb7af7c8" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentDomain_019c43d6-dc8d-7ef9-8819-0035cb7af7c8_default" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_dei_DocumentInformationDocumentAxis_019c43d6-dc8d-7ef9-8819-0035cb7af7c8" xlink:to="loc_dei_DocumentDomain_019c43d6-dc8d-7ef9-8819-0035cb7af7c8_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentDomain_019c43d6-dc8d-7ff6-b91e-c1c9e6f3112a" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_dei_DocumentInformationDocumentAxis_019c43d6-dc8d-7ef9-8819-0035cb7af7c8" xlink:to="loc_dei_DocumentDomain_019c43d6-dc8d-7ff6-b91e-c1c9e6f3112a" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType_019c43d6-dc8d-75d2-9fa8-a41329e8c696" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentType"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_DocumentType_019c43d6-dc8d-75d2-9fa8-a41329e8c696" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate_019c43d6-dc8d-763f-88e6-02fad062d019" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentPeriodEndDate"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_DocumentPeriodEndDate_019c43d6-dc8d-763f-88e6-02fad062d019" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName_019c43d6-dc8d-7450-93b2-1a45c1458cf2" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityRegistrantName"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityRegistrantName_019c43d6-dc8d-7450-93b2-1a45c1458cf2" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode_019c43d6-dc8d-7042-bee7-3b0e713f7c8d" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityIncorporationStateCountryCode_019c43d6-dc8d-7042-bee7-3b0e713f7c8d" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber_019c43d6-dc8d-7ac1-98f7-1debb072a3dd" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityFileNumber"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityFileNumber_019c43d6-dc8d-7ac1-98f7-1debb072a3dd" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber_019c43d6-dc8d-771e-a835-1c1e59c3ca9b" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityTaxIdentificationNumber_019c43d6-dc8d-771e-a835-1c1e59c3ca9b" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2_019c43d6-dc8d-7bd3-8328-2085865cdee5" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressAddressLine2"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityAddressAddressLine2_019c43d6-dc8d-7bd3-8328-2085865cdee5" xlink:type="arc" order="6"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode_019c43d6-dc8d-78d5-a9e0-478d699f2a1d" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressPostalZipCode"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityAddressPostalZipCode_019c43d6-dc8d-78d5-a9e0-478d699f2a1d" xlink:type="arc" order="7"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince_019c43d6-dc8d-74e1-87f5-c29341854db7" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressStateOrProvince"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityAddressStateOrProvince_019c43d6-dc8d-74e1-87f5-c29341854db7" xlink:type="arc" order="8"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown_019c43d6-dc8d-7c03-9ff6-865494e8dd4c" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressCityOrTown"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityAddressCityOrTown_019c43d6-dc8d-7c03-9ff6-865494e8dd4c" xlink:type="arc" order="9"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1_019c43d6-dc8d-7079-b604-cf8b1e827bb2" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressAddressLine1"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityAddressAddressLine1_019c43d6-dc8d-7079-b604-cf8b1e827bb2" xlink:type="arc" order="10"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber_019c43d6-dc8d-7d73-a410-01d9d992f957" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_LocalPhoneNumber"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_LocalPhoneNumber_019c43d6-dc8d-7d73-a410-01d9d992f957" xlink:type="arc" order="11"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode_019c43d6-dc8d-78da-8393-276612cf76f1" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_CityAreaCode"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_CityAreaCode_019c43d6-dc8d-78da-8393-276612cf76f1" xlink:type="arc" order="12"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_WrittenCommunications_019c43d6-dc8d-7588-8a47-dde3253ec36f" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_WrittenCommunications"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_WrittenCommunications_019c43d6-dc8d-7588-8a47-dde3253ec36f" xlink:type="arc" order="13"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SolicitingMaterial_019c43d6-dc8d-7f6b-bf52-62672caf638f" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_SolicitingMaterial"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_SolicitingMaterial_019c43d6-dc8d-7f6b-bf52-62672caf638f" xlink:type="arc" order="14"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_PreCommencementTenderOffer_019c43d6-dc8d-7af4-be93-761c2ead1f1f" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_PreCommencementTenderOffer"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_PreCommencementTenderOffer_019c43d6-dc8d-7af4-be93-761c2ead1f1f" xlink:type="arc" order="15"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_PreCommencementIssuerTenderOffer_019c43d6-dc8d-73bd-8948-80c9b1590b33" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_PreCommencementIssuerTenderOffer"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_PreCommencementIssuerTenderOffer_019c43d6-dc8d-73bd-8948-80c9b1590b33" xlink:type="arc" order="16"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_Security12bTitle_019c43d6-dc8d-7929-beb5-a22805282aa1" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_Security12bTitle"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_Security12bTitle_019c43d6-dc8d-7929-beb5-a22805282aa1" xlink:type="arc" order="17"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol_019c43d6-dc8d-7e89-b62c-32f261ff9898" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_TradingSymbol"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_TradingSymbol_019c43d6-dc8d-7e89-b62c-32f261ff9898" xlink:type="arc" order="18"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName_019c43d6-dc8d-7e59-b873-905816b4cc7e" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_SecurityExchangeName"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_SecurityExchangeName_019c43d6-dc8d-7e59-b873-905816b4cc7e" xlink:type="arc" order="19"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag_019c43d6-dc8d-776a-b634-bd75d496ccbc" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_AmendmentFlag"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_AmendmentFlag_019c43d6-dc8d-776a-b634-bd75d496ccbc" xlink:type="arc" order="20"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey_019c43d6-dc8d-7d8d-896e-c3743c281621" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityCentralIndexKey"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityCentralIndexKey_019c43d6-dc8d-7d8d-896e-c3743c281621" xlink:type="arc" order="21"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany_019c43d6-dc8d-72e7-a9c6-01d077c2bf36" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_EntityEmergingGrowthCompany_019c43d6-dc8d-72e7-a9c6-01d077c2bf36" xlink:type="arc" order="22"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentDescription_019ce223-4f72-7280-863c-cfc908d73efc" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_AmendmentDescription"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_DocumentInformationLineItems_019c43d6-dc8d-732e-a8c2-b049a348c5bd" xlink:to="loc_dei_AmendmentDescription_019ce223-4f72-7280-863c-cfc908d73efc" xlink:type="arc" order="23"/>
  </link:definitionLink>
</link:linkbase>
