<SEC-DOCUMENT>0001104659-25-046877.txt : 20250509
<SEC-HEADER>0001104659-25-046877.hdr.sgml : 20250509
<ACCEPTANCE-DATETIME>20250509182043
ACCESSION NUMBER:		0001104659-25-046877
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20250508
FILED AS OF DATE:		20250509
DATE AS OF CHANGE:		20250509

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Horowitz Joshua
		CENTRAL INDEX KEY:			0001612424
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		25932066

	MAIL ADDRESS:	
		STREET 1:		72-38 113TH STREET
		STREET 2:		APARTMENT 3L
		CITY:			FOREST HILLS
		STATE:			NY
		ZIP:			11375

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			KINGSWAY FINANCIAL SERVICES INC
		CENTRAL INDEX KEY:			0001072627
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		ORGANIZATION NAME:           	02 Finance
		EIN:				999999999
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
		BUSINESS PHONE:		(312) 766-2144

	MAIL ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>tm2514705-1_4seq1.xml
<DESCRIPTION>OWNERSHIP DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2025-05-08</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0001072627</issuerCik>
        <issuerName>KINGSWAY FINANCIAL SERVICES INC</issuerName>
        <issuerTradingSymbol>KFS</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001612424</rptOwnerCik>
            <rptOwnerName>Horowitz Joshua</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O PALM MANAGEMENT (US) LLC</rptOwnerStreet1>
            <rptOwnerStreet2>19 WEST ELM STREET</rptOwnerStreet2>
            <rptOwnerCity>GREENWICH</rptOwnerCity>
            <rptOwnerState>CT</rptOwnerState>
            <rptOwnerZipCode>06830</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle></officerTitle>
            <otherText></otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Class D Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.50</value>
                <footnoteId id="F1"/>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2025-05-08</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>14000</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>25</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <value>2025-05-08</value>
                <footnoteId id="F1"/>
            </exerciseDate>
            <expirationDate>
                <value>2032-05-08</value>
                <footnoteId id="F1"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>36842.4</value>
                    <footnoteId id="F1"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>14000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Palm Global Small Cap Master Fund LP</value>
                    <footnoteId id="F2"/>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeTransaction>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">The shares of Class D Preferred Stock, par value $0.01 per share (the &quot;Class D Preferred Stock&quot;), of Kingsway Financial Services Inc. (the &quot;Company&quot;) have a stated value of $25 per share and are convertible at any time, at the holder's option, into shares of Common Stock, par value $0.01 per share, of the Company (the &quot;Common Stock&quot;) at an initial conversion price of $9.50 per share (or 2.6316 shares of Common Stock for each share of Class D Preferred Stock), subject to customary adjustments. The Company has the option to redeem 25% of the outstanding shares of Class D Preferred Stock for cash upon the occurrence of certain events. All then-outstanding shares of Class D Preferred Stock shall be redeemed by the Company for cash on May 8, 2032.</footnote>
        <footnote id="F2">Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP (&quot;Palm Global&quot;), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Joshua Horowitz</signatureName>
        <signatureDate>2025-05-09</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
