Sec Form 4 Filing - STILWELL JOSEPH @ KINGSWAY FINANCIAL SERVICES INC - 2025-02-12

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person STILWELL JOSEPH 2. Issuer Name and Ticker or Trading Symbol KINGSWAY FINANCIAL SERVICES INC [ KFS] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 200 CALLE DEL SANTO CRISTO 3. Date of Earliest Transaction (MM/DD/YY) 02/12/2025 (Street) SAN JUAN, PR00901 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 162,500 ( 1 ) D Common Stock 4,309,472 I See footnote ( 2 ) Common Stock 567,612 I See footnote ( 3 ) Common Stock 918,786 I See footnote ( 4 ) Common Stock 904,657 I See footnote ( 5 )

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Class C Preferred Stock $ 9.5 ( 6 ) 02/12/2025 A 33,600 02/12/2025 02/12/2032( 6 ) Common Stock 88,421 ( 6 ) $ 25 33,600 I See footnote ( 2 ) Class C Preferred Stock $ 9.5 ( 6 ) 02/12/2025 A 6,400 02/12/2025 02/12/2032( 6 ) Common Stock 16,842 ( 6 ) $ 25 6,400 I See footnote ( 3 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other STILWELL JOSEPH 200 CALLE DEL SANTO CRISTO SAN JUAN, PR00901 X X Stilwell Value LLC 111 BROADWAY, 12TH FLOOR NEW YORK, NY10006 X STILWELL ASSOCIATES L P 111 BROADWAY, 12TH FLOOR NEW YORK, NY10006 X Stilwell Activist Fund, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY10006 X Stilwell Activist Investments, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY10006 X Stilwell Value Partners VII, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY10006 X Signatures /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell 02/14/2025 Signature of Reporting Person Date /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC 02/14/2025 Signature of Reporting Person Date /s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P. 02/14/2025 Signature of Reporting Person Date /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P. 02/14/2025 Signature of Reporting Person Date /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P. 02/14/2025 Signature of Reporting Person Date /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 02/14/2025 Signature of Reporting Person Date

Explanation of Responses:

( 1 )These are shares owned directly by Joseph Stilwell. ( 2 )These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("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. ( 3 )These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") 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. ( 4 )These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") 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. ( 5 )These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, 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. ( 6 )The shares of Class C Preferred Stock of Kingsway Financial Services Inc. (the "Company") 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 "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.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

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