<SEC-DOCUMENT>0001127602-25-004901.txt : 20250214
<SEC-HEADER>0001127602-25-004901.hdr.sgml : 20250214
<ACCEPTANCE-DATETIME>20250214161256
ACCESSION NUMBER:		0001127602-25-004901
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20250213
FILED AS OF DATE:		20250214
DATE AS OF CHANGE:		20250214

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Kavanagh Terence Michael
		CENTRAL INDEX KEY:			0001538185
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		25628801

	MAIL ADDRESS:	
		STREET 1:		OAKMONT CAPITAL INC.
		STREET 2:		45 ST. CLAIR AVENUE WEST, SUITE 400
		CITY:			TORONTO
		STATE:			A6
		ZIP:			M4V 1K9

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
		IRS NUMBER:				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>form4.xml
<DESCRIPTION>PRIMARY DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2025-02-13</periodOfReport>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001538185</rptOwnerCik>
            <rptOwnerName>Kavanagh Terence Michael</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>OAKMONT CAPITAL INC.</rptOwnerStreet1>
            <rptOwnerStreet2>45 ST. CLAIR AVENUE WEST, SUITE 400</rptOwnerStreet2>
            <rptOwnerCity>TORONTO</rptOwnerCity>
            <rptOwnerState>A6</rptOwnerState>
            <rptOwnerZipCode>M4V 1K9</rptOwnerZipCode>
            <rptOwnerStateDescription>ONTARIO, CANADA</rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Class C Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>9.50</value>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2025-02-13</value>
                <footnoteId id="F1"/>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>40000</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>25.00</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <value>2025-02-13</value>
            </exerciseDate>
            <expirationDate>
                <value>2032-02-12</value>
                <footnoteId id="F1"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>105263.2</value>
                    <footnoteId id="F1"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>40000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>By Oakmont Capital Inc.</value>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeTransaction>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">The shares of Class C 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 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/ Debra S. Rouse, attorney-in-fact for Terence Michael Kavanagh</signatureName>
        <signatureDate>2025-02-14</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
