<SEC-DOCUMENT>0001958244-25-004571.txt : 20251223
<SEC-HEADER>0001958244-25-004571.hdr.sgml : 20251223
<ACCEPTANCE-DATETIME>20251223165854
ACCESSION NUMBER:		0001958244-25-004571
CONFORMED SUBMISSION TYPE:	144
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20251223
DATE AS OF CHANGE:		20251223

SUBJECT COMPANY:	

	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

	FILING VALUES:
		FORM TYPE:		144
		SEC ACT:		1933 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		251601504

	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

REPORTING-OWNER:	

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Fitzgerald John Taylor Maloney
		CENTRAL INDEX KEY:			0001584349
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		144

	MAIL ADDRESS:	
		STREET 1:		KINGSWAY FINANCIAL SERVICES INC.
		STREET 2:		150 PIERCE ROAD, SUITE 600
		CITY:			ITASCA
		STATE:			IL
		ZIP:			60143
</SEC-HEADER>
<DOCUMENT>
<TYPE>144
<SEQUENCE>1
<FILENAME>primary_doc.xml
<TEXT>
<XML>
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    <ns2:headerData>
        <ns2:submissionType>144</ns2:submissionType>
        <ns2:filerInfo>
            <ns2:filer>
                <ns2:filerCredentials>
                    <ns2:cik>0001584349</ns2:cik>
                    <ns2:ccc>XXXXXXXX</ns2:ccc>
                </ns2:filerCredentials>
            </ns2:filer>
            <ns2:liveTestFlag>LIVE</ns2:liveTestFlag>



        </ns2:filerInfo>
    </ns2:headerData>
    <ns2:formData>
        <ns2:issuerInfo>
            <ns2:issuerCik>0001072627</ns2:issuerCik>
            <ns2:issuerName>KINGSWAY FINANCIAL SERVICES INC.</ns2:issuerName>
            <ns2:secFileNumber>001-15204</ns2:secFileNumber>
            <ns2:issuerAddress>
                <com:street1>10 S. Riverside Plaza</com:street1>
                <com:street2>Suite 1520</com:street2>
                <com:city>Chicago</com:city>
                <com:stateOrCountry>IL</com:stateOrCountry>
                <com:zipCode>60606</com:zipCode>
            </ns2:issuerAddress>
            <ns2:issuerContactPhone>1-312-766-2138</ns2:issuerContactPhone>
            <ns2:nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>John T. Fitzgerald</ns2:nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
            <ns2:relationshipsToIssuer>
                <ns2:relationshipToIssuer>Officer</ns2:relationshipToIssuer>
            </ns2:relationshipsToIssuer>
        </ns2:issuerInfo>
        <ns2:securitiesInformation>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:brokerOrMarketmakerDetails>
                <ns2:name>Goldman Sachs &amp; Co. LLC</ns2:name>
                <ns2:address>
                    <com:street1>200 West Street</com:street1>
                    <com:city>New York</com:city>
                    <com:stateOrCountry>NY</com:stateOrCountry>
                    <com:zipCode>10282</com:zipCode>
                </ns2:address>
            </ns2:brokerOrMarketmakerDetails>
            <ns2:noOfUnitsSold>30000</ns2:noOfUnitsSold>
            <ns2:aggregateMarketValue>398400</ns2:aggregateMarketValue>
            <ns2:noOfUnitsOutstanding>28956152</ns2:noOfUnitsOutstanding>
            <ns2:approxSaleDate>12/23/2025</ns2:approxSaleDate>
            <ns2:securitiesExchangeName>NYSE</ns2:securitiesExchangeName>
        </ns2:securitiesInformation>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>08/02/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>70</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>08/02/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>08/17/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>100</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>08/17/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>08/22/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>500</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>08/22/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>08/23/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>2380</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>08/23/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/27/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>4466</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/27/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>08/01/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>4979</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>08/01/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/07/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>3395</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/07/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/12/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>3049</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/12/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/26/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>4466</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/26/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/13/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>3049</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/13/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/06/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>3395</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/06/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:securitiesToBeSold>
            <ns2:securitiesClassTitle>Common</ns2:securitiesClassTitle>
            <ns2:acquiredDate>07/01/2016</ns2:acquiredDate>
            <ns2:natureOfAcquisitionTransaction>Acquired as compensation -- Restricted Stock Units</ns2:natureOfAcquisitionTransaction>
            <ns2:nameOfPersonfromWhomAcquired>Issuer</ns2:nameOfPersonfromWhomAcquired>
            <ns2:isGiftTransaction>N</ns2:isGiftTransaction>
            <ns2:amountOfSecuritiesAcquired>151</ns2:amountOfSecuritiesAcquired>
            <ns2:paymentDate>07/01/2016</ns2:paymentDate>
            <ns2:natureOfPayment>Compensation</ns2:natureOfPayment>
        </ns2:securitiesToBeSold>
        <ns2:nothingToReportFlagOnSecuritiesSoldInPast3Months>Y</ns2:nothingToReportFlagOnSecuritiesSoldInPast3Months>
        <ns2:noticeSignature>
            <ns2:noticeDate>12/23/2025</ns2:noticeDate>
            <ns2:planAdoptionDates/>
            <ns2:signature>Goldman Sachs &amp; Co. LLC on behalf of John T. Fitzgerald</ns2:signature>
        </ns2:noticeSignature>
    </ns2:formData>
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</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
