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SEC EDGAR · Insider purchase

SKWD: Kuczinski Anthony J reported buying shares

3 reported purchases of non-derivative securities. Code P includes open-market and private purchases; it does not establish motive.

Follow SKWD
Became public
May 21, 2026, 5:27 PM EDT
Event / period date
May 21, 2026
Collected
Nov 10, 2026, 2:07 PM EST

Why this is connected

This filing identifies Skyward Specialty Insurance Group, Inc. as the issuer of the security. The company's SEC identifier connects it to SKWD.

Open the original source ↗Follow company activity in SKWD

Reported transactions

Kuczinski Anthony J (Director)

200 shares · Common Stock

May 21, 2026 · $47.00 per share

800 shares · Common Stock

May 21, 2026 · $47.00 per share

1,000 shares · Common Stock

May 21, 2026 · $47.20 per share

Value calculated from the reported shares and prices: $94,200.00.

Code P covers open-market and private purchases. Grants, option exercises, and tax withholding are excluded from purchase results. Read the source footnotes for ownership and pricing details.

Source evidence

Read the source excerpt or record
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0609</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2026-05-21</periodOfReport>

    <issuer>
        <issuerCik>0001519449</issuerCik>
        <issuerName>Skyward Specialty Insurance Group, Inc.</issuerName>
        <issuerTradingSymbol>SKWD</issuerTradingSymbol>
        <issuerForeignTradingSymbol></issuerForeignTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001976607</rptOwnerCik>
            <rptOwnerName>Kuczinski Anthony J</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerNonUSAddressFlag>false</rptOwnerNonUSAddressFlag>
            <rptOwnerStreet1>800 GESSNER ROAD</rptOwnerStreet1>
            <rptOwnerStreet2>SUITE 600</rptOwnerStreet2>
            <rptOwnerCity>HOUSTON</rptOwnerCity>
            <rptOwnerState>TX</rptOwnerState>
            <rptOwnerZipCode>77024</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>true</isDirector>
            <isOfficer>false</isOfficer>
            <isTenPercentOwner>false</isTenPercentOwner>
            <isOther>false</isOther>
            <officerTitle></officerTitle>
            <otherText></otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2026-05-21</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>200</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>47</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>14177</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2026-05-21</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>800</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>47</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>14977</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2026-05-21</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>1000</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>47.20</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>15977</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable></derivativeTable>

    <footnotes></footnotes>

    <ownerSignature>
        <signatureName>/s/ Stacy E. Skelton, Attorney-in-Fact</signatureName>
        <signatureDate>2026-05-21</signatureDate>
    </ownerSignature>
</ownershipDocument>

Price change after we could observe it

+1.24% SKWD

Adjusted closing prices from Nov 11, 2026 to Nov 12, 2026. The start is the first available close after both publication and collection. This is a price comparison, not an executed trade, investor profit, or a backtested strategy.

Congressional trading in SKWD

These disclosures provide context. Their presence does not establish a link between a trader and the event.

Original documents control. Public records can be amended, and company connections may require interpretation. Nothing here is investment advice.