<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2026-01-08</periodOfReport>

    <issuer>
        <issuerCik>0001393726</issuerCik>
        <issuerName>TIPTREE INC.</issuerName>
        <issuerTradingSymbol>TIPT</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001648181</rptOwnerCik>
            <rptOwnerName>Friedman Paul M</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O TIPTREE INC.</rptOwnerStreet1>
            <rptOwnerStreet2>660 STEAMBOAT ROAD</rptOwnerStreet2>
            <rptOwnerCity>GREENWICH</rptOwnerCity>
            <rptOwnerState>CT</rptOwnerState>
            <rptOwnerZipCode>06830</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>true</isDirector>
            <isOfficer>false</isOfficer>
            <isTenPercentOwner>false</isTenPercentOwner>
            <isOther>false</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>false</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2026-01-08</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>false</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>2048</value>
                    <footnoteId id="F1"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>122398</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>By The Paul M. Friedman Living Trust</value>
                    <footnoteId id="F2"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.</footnote>
        <footnote id="F2">At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the &quot;Living Trust&quot;), of which the Reporting Person and his spouse are trustees.</footnote>
    </footnotes>

    <remarks>Exhibit List: Exhibit 24-Power of Attorney</remarks>

    <ownerSignature>
        <signatureName>/s/ Siew Kwok, as Attorney-in-fact for Paul M. Friedman</signatureName>
        <signatureDate>2026-01-09</signatureDate>
    </ownerSignature>
</ownershipDocument>
