<SEC-DOCUMENT>0001104659-25-122549.txt : 20251218
<SEC-HEADER>0001104659-25-122549.hdr.sgml : 20251218
<ACCEPTANCE-DATETIME>20251218161519
ACCESSION NUMBER:		0001104659-25-122549
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20251217
FILED AS OF DATE:		20251218
DATE AS OF CHANGE:		20251218

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:		251583262

	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>tm2533539-2_4seq1.xml
<DESCRIPTION>OWNERSHIP DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2025-12-17</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>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-12-17</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>X</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>22500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>8.25</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>32500</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-12-17</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>X</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>252500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>8.25</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>367500</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>by Palm Global Small Cap Master Fund LP</value>
                    <footnoteId id="F2"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Stock Option (Right to Buy)</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>8.25</value>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2025-12-17</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>X</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>22500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <footnoteId id="F3"/>
            </exerciseDate>
            <expirationDate>
                <value>2025-12-29</value>
                <footnoteId id="F3"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>22500</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>0</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeTransaction>
        <derivativeTransaction>
            <securityTitle>
                <value>Stock Option (Right to Buy)</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>8.25</value>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2025-12-17</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>X</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>252500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <footnoteId id="F3"/>
            </exerciseDate>
            <expirationDate>
                <value>2025-12-29</value>
                <footnoteId id="F3"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>252500</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>0</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>by Palm Global Small Cap Master Fund LP</value>
                    <footnoteId id="F2"/>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeTransaction>
        <derivativeHolding>
            <securityTitle>
                <value>Class D Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.5</value>
                <footnoteId id="F1"/>
            </conversionOrExercisePrice>
            <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>
        </derivativeHolding>
    </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>
        <footnote id="F3">On March 31, 2025, Mr. Horowitz and Palm Global entered into an option agreement with Stilwell Value LLC, (the &quot;Option Agreement&quot;) to acquire 22,500 and 252,500 shares of Common Stock, respectively, at an exercise price of $8.25 per share, which Option Agreement was amended on December 17, 2025, to allow for the early exercise of the options. The options had an expiration of December 29, 2025 at 5:00 p.m. Eastern Time.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Joshua Horowitz</signatureName>
        <signatureDate>2025-12-18</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
