SEC FORM 4

SEC FORM 4 SEC Form 4

FORM 4

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
or Section 30(h) of the Investment Company Act of 1940

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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 for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Stilwell Joseph

(Last)

(First)

(Middle)

200 CALLE DEL SANTO CRISTO

(Street)

SAN JUAN

00901

(City)

(State)

(Zip)

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)

3. Date of Earliest Transaction (Month/Day/Year)
12/17/2025

4. If Amendment, Date of 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

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
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⁾

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 Securities Underlying Derivative Security (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: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Class D Preferred Stock	$9.5⁽⁷⁾							05/07/2025	05/07/2032⁽⁷⁾	Common Stock	52,631⁽⁷⁾		20,000	I	See footnote⁽³⁾
Class C Preferred Stock	$9.5⁽⁸⁾							02/12/2025	02/12/2032⁽⁸⁾	Common Stock	88,421⁽⁸⁾		33,600	I	See footnote⁽⁴⁾
Class C Preferred Stock	$9.5⁽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⁾

1. Name and Address of Reporting Person^*

Stilwell Joseph

(Last)

(First)

(Middle)

200 CALLE DEL SANTO CRISTO

(Street)

SAN JUAN

00901

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

X	Director	X	10% Owner
	Officer (give title below)		Other (specify below)

1. Name and Address of Reporting Person^*

Stilwell Value LLC

(Last)

(First)

(Middle)

111 BROADWAY, 12TH FLOOR

(Street)

NEW YORK

10006

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director	X	10% Owner
Officer (give title below)		Other (specify below)

1. Name and Address of Reporting Person^*

Stilwell Associates, L.P.

(Last)

(First)

(Middle)

111 BROADWAY, 12TH FLOOR

(Street)

NEW YORK

10006

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director	X	10% Owner
Officer (give title below)		Other (specify below)

1. Name and Address of Reporting Person^*

Stilwell Activist Fund, L.P.

(Last)

(First)

(Middle)

111 BROADWAY, 12TH FLOOR

(Street)

NEW YORK

10006

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director	X	10% Owner
Officer (give title below)		Other (specify below)

1. Name and Address of Reporting Person^*

Stilwell Activist Investments, L.P.

(Last)

(First)

(Middle)

111 BROADWAY, 12TH FLOOR

(Street)

NEW YORK

10006

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director	X	10% Owner
Officer (give title below)		Other (specify below)

1. Name and Address of Reporting Person^*

Stilwell Value Partners VII, L.P.

(Last)

(First)

(Middle)

111 BROADWAY, 12TH FLOOR

(Street)

NEW YORK

10006

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director	X	10% Owner
Officer (give title below)		Other (specify below)

Explanation of Responses:

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.

	/s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell	12/19/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC	12/19/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.	12/19/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.	12/19/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.	12/19/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	12/19/2025
	** Signature of Reporting Person	Date
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).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

SEC Form 4 filed by Director Stilwell Joseph