Kingsway (KFS) insider Stilwell reports stock sale and preferred stakes

Rhea-AI Filing Summary

Kingsway Financial Services Inc. insider Joseph Stilwell, a director and 10% owner, reported a sale of Common Stock. On 12/22/2025, Stilwell Associates, L.P. sold 19,229 shares of Kingsway common stock at $12.80 per share.

After this transaction, Stilwell reports 162,500 shares owned directly and additional indirect holdings of Kingsway common stock through several investment entities, including 300,000, 2,254,971, 436,911 and 371,568 shares. He also reports indirect interests in Kingsway preferred stock: Class D and Class C series with stated value of $25 per share, convertible into common stock at 2.63158 common shares per preferred share, with underlying amounts of 52,631, 88,421 and 16,842 common shares and redemption dates in 2032 as disclosed.

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

OMB APPROVAL

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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 PR 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)
12/22/2025

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock								162,500(1)	D
Common Stock	12/22/2025		S(2)		19,229	D	$12.8	300,000	I	See footnote(3)
Common Stock								2,254,971	I	See footnote(4)
Common Stock								436,911	I	See footnote(5)
Common Stock								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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
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)

1. Name and Address of Reporting Person^*

Stilwell Joseph

(Last) (First) (Middle)

200 CALLE DEL SANTO CRISTO

(Street)

SAN JUAN PR 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 NY 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 NY 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 NY 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 NY 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 NY 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. This Form 4 reports the following sales: on December 22, 2025, Stilwell Associates, L.P. ("Associates") sold 19,229 shares at $12.80.

3. These are shares owned directly by Associates 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 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 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 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	12/29/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC	12/29/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.	12/29/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.	12/29/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.	12/29/2025
	/s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	12/29/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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FAQ

What insider transaction was reported for Kingsway Financial Services Inc. (KFS)?

The filing reports that on 12/22/2025, Stilwell Associates, L.P., related to insider Joseph Stilwell, sold 19,229 shares of Kingsway Financial Services Inc. common stock at $12.80 per share.

What is Joseph Stilwells relationship to Kingsway Financial Services Inc. (KFS)?

Joseph Stilwell is reported as both a Director and a 10% Owner of Kingsway Financial Services Inc., reflecting significant insider ownership and board-level involvement.

How many Kingsway (KFS) shares does Joseph Stilwell report owning after the transaction?

After the reported sale, Stilwell lists 162,500 shares of common stock owned directly, and indirect holdings of 300,000, 2,254,971, 436,911 and 371,568 Kingsway common shares through various investment partnerships.

Which entities hold Kingsway (KFS) shares indirectly for Joseph Stilwell?

Indirect holdings are reported through Stilwell Associates, L.P., Stilwell Activist Investments, L.P., Stilwell Activist Fund, L.P. and Stilwell Value Partners VII, L.P., with Joseph Stilwell linked via Stilwell Value LLC as general partner.

What preferred stock positions related to Kingsway (KFS) does Joseph Stilwell report?

The filing shows interests in Class D Preferred Stock and Class C Preferred Stock of Kingsway, each with a stated value of $25 per share and convertible into common stock at a rate of 2.63158 common shares per preferred share, with underlying amounts of 52,631, 88,421 and 16,842 common shares.

When are Kingsway (KFS) preferred shares reported to be redeemed?

The filing states that all outstanding Class D Preferred Stock shall be redeemed on May 7, 2032, and all outstanding Class C Preferred Stock shall be redeemed on February 12, 2032.