<SEC-DOCUMENT>0001104659-25-121276.txt : 20251215
<SEC-HEADER>0001104659-25-121276.hdr.sgml : 20251215
<ACCEPTANCE-DATETIME>20251215183009
ACCESSION NUMBER:		0001104659-25-121276
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20251211
FILED AS OF DATE:		20251215
DATE AS OF CHANGE:		20251215

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Associates, L.P.
		CENTRAL INDEX KEY:			0000913960
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572881

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		212-269-2005

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

	FORMER NAME:	
		FORMER CONFORMED NAME:	STILWELL ASSOCIATES L P
		DATE OF NAME CHANGE:	19931022

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Value LLC
		CENTRAL INDEX KEY:			0001397076
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572882

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		2122692005

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Joseph
		CENTRAL INDEX KEY:			0001113303
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572883

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

	FORMER NAME:	
		FORMER CONFORMED NAME:	STILWELL JOSEPH
		DATE OF NAME CHANGE:	20000502

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Activist Investments, L.P.
		CENTRAL INDEX KEY:			0001573720
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572879

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		2122692005

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Value Partners VII, L.P.
		CENTRAL INDEX KEY:			0001555931
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572878

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		2122692005

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Activist Fund, L.P.
		CENTRAL INDEX KEY:			0001564452
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251572880

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		2122692005

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

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>
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<SEQUENCE>1
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    <periodOfReport>2025-12-11</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001113303</rptOwnerCik>
            <rptOwnerName>Stilwell Joseph</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>200 CALLE DEL SANTO CRISTO</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>SAN JUAN</rptOwnerCity>
            <rptOwnerState>PR</rptOwnerState>
            <rptOwnerZipCode>00901</rptOwnerZipCode>
            <rptOwnerStateDescription>PUERTO RICO</rptOwnerStateDescription>
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    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001397076</rptOwnerCik>
            <rptOwnerName>Stilwell Value LLC</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
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    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0000913960</rptOwnerCik>
            <rptOwnerName>Stilwell Associates, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
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        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001564452</rptOwnerCik>
            <rptOwnerName>Stilwell Activist Fund, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
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    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001573720</rptOwnerCik>
            <rptOwnerName>Stilwell Activist Investments, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
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            <otherText></otherText>
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    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001555931</rptOwnerCik>
            <rptOwnerName>Stilwell Value Partners VII, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
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        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>162500</value>
                    <footnoteId id="F1"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-12-11</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F2"/>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>67500</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>12.80</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>579404</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F3"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>3550382</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F4"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>457181</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F5"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>590410</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F6"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeHolding>
            <securityTitle>
                <value>Class D Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.5</value>
                <footnoteId id="F7"/>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2025-05-07</value>
            </exerciseDate>
            <expirationDate>
                <value>2032-05-07</value>
                <footnoteId id="F7"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>52631</value>
                    <footnoteId id="F7"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>20000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F3"/>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeHolding>
        <derivativeHolding>
            <securityTitle>
                <value>Class C Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.5</value>
                <footnoteId id="F8"/>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2025-02-12</value>
            </exerciseDate>
            <expirationDate>
                <value>2032-02-12</value>
                <footnoteId id="F8"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>88421</value>
                    <footnoteId id="F8"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>33600</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F4"/>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeHolding>
        <derivativeHolding>
            <securityTitle>
                <value>Class C Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.5</value>
                <footnoteId id="F8"/>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2025-02-12</value>
            </exerciseDate>
            <expirationDate>
                <value>2032-02-12</value>
                <footnoteId id="F8"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>16842</value>
                    <footnoteId id="F8"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>6400</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F5"/>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeHolding>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">These are shares owned directly by Joseph Stilwell.</footnote>
        <footnote id="F2">This Form 4 reports the following sales: on December 11, 2025 Stilwell Associates, L.P. (&quot;Associates&quot;) sold 67,500 shares at $12.80.</footnote>
        <footnote id="F3">These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC (&quot;Value&quot;), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.</footnote>
        <footnote id="F4">These are shares owned directly by Stilwell Activist Investments, L.P. (&quot;SAI&quot;) and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.</footnote>
        <footnote id="F5">These are shares owned directly by Stilwell Activist Fund, L.P. (&quot;SAF&quot;) and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.</footnote>
        <footnote id="F6">These are shares owned directly by Stilwell Value Partners VII, L.P. (&quot;SVP VII&quot;) and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.</footnote>
        <footnote id="F7">The shares of Class D Preferred Stock of Kingsway Financial Services Inc. (the &quot;Company&quot;) have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the &quot;Common Stock&quot;) at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032.</footnote>
        <footnote id="F8">The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.</signatureName>
        <signatureDate>2025-12-15</signatureDate>
    </ownerSignature>
</ownershipDocument>
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