FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b). Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 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 (Month/Day/Year) 12/17/2025 (Street) SAN JUAN, PR 00901 4. If Amendment, Date Original Filed (Month/Day/Year) 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 (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 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 12/17/2025 X(2) 215,477 D $8.25 319,229 I See footnote(3) Common Stock 12/17/2025 X(2) 1,295,411 D $8.25 2,254,971 I See footnote(4) Common Stock 12/17/2025 X(2) 20,270 D $8.25 436,911 I See footnote(5) Common Stock 12/17/2025 X(2) 218,842 D $8.25 371,568 I See footnote(6)

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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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 (Month/Day/Year)

3A. Deemed Execution Date, if any (Month/Day/Year)

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 (Month/Day/Year)

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 D Preferred Stock

$9.50(7)

05/07/2025

05/07/2032(7)

Common Stock

52,631(7)

20,000

I

See footnote(3)

Class C Preferred Stock

$9.50(8)

02/12/2025

02/12/2032(8)

Common Stock

88,421(8)

33,600

I

See footnote(4)

Class C Preferred Stock

$9.50(8)

02/12/2025

02/12/2032(8)

Common Stock

16,842(8)

6,400

I

See footnote(5)

Stock Option (obligation to sell)

$8.25

12/17/2025

X(2)

215,477

(2)

12/29/2025(2)

Common Stock

215,477

$ 0

0

I

See footnote(3)

Stock Option (obligation to sell)

$8.25

12/17/2025

X(2)

1,295,411

(2)

12/29/2025(2)

Common Stock

1,295,411

$ 0

0

I

See footnote(4)

Stock Option (obligation to sell)

$8.25

12/17/2025

X(2)

20,270

(2)

12/29/2025(2)

Common Stock

20,270

$ 0

0

I

See footnote(5)

Stock Option (obligation to sell)

$8.25

12/17/2025

X(2)

218,842

(2)

12/29/2025(2)

Common Stock

218,842

$ 0

0

I

See footnote(6)

Reporting Owners

Reporting Owner Name / Address	Relationships
	Director	10% Owner	Officer	Other
Stilwell Joseph 200 CALLE DEL SANTO CRISTO SAN JUAN, PR 00901	X	X
Stilwell Value LLC 111 BROADWAY, 12TH FLOOR NEW YORK, NY 10006		X
Stilwell Associates, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY 10006		X
Stilwell Activist Fund, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY 10006		X
Stilwell Activist Investments, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY 10006		X
Stilwell Value Partners VII, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK, NY 10006		X

Signatures

/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell		12/19/2025
**Signature of Reporting Person		Date
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC		12/19/2025
**Signature of Reporting Person		Date
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.		12/19/2025
**Signature of Reporting Person		Date
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.		12/19/2025
**Signature of Reporting Person		Date
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.		12/19/2025
**Signature of Reporting Person		Date
/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.		12/19/2025
**Signature of Reporting Person		Date

Explanation of Responses:

*	If the form is filed by more than one reporting person, see Instruction 4(b)(v).
**	Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1)	These are shares owned directly by Joseph Stilwell.
(2)	On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.
(3)	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.
(4)	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 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.
(5)	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.
(6)	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.
(7)	The shares of Class D 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 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.
(8)	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.

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