Kingsway Financial (KFS) insider Stilwell reports 55,000-share sale and large holdings

Rhea-AI Filing Summary

Kingsway Financial Services Inc. insider activity: Director and 10% owner Joseph Stilwell, reporting jointly with several Stilwell investment partnerships, disclosed open-market sales of a total of 55,000 shares of Kingsway common stock. Stilwell Associates, L.P. sold 35,000 shares on December 8, 2025 at $12.82 per share and 20,000 shares on December 9, 2025 at $12.80 per share.

Following these trades, Stilwell Associates reports indirect beneficial ownership of 646,904 common shares, while other Stilwell entities report additional indirect holdings of 3,550,382, 457,181 and 590,410 common shares. The group also reports Class C and Class D preferred stock that is convertible into common stock at 2.63158 common shares per preferred share, with all outstanding Class D preferred to be redeemed on May 7, 2032 and all outstanding Class C preferred to be redeemed on February 12, 2032. Stilwell disclaims beneficial ownership of indirectly held shares except to the extent of his pecuniary interest.

Insights

Equity Ownership and Governance Analyst

Insider group sold a small block of common shares but retains a large, complex equity and convertible preferred stake in the company.

The filing shows entities affiliated with Joseph Stilwell, a director and 10% owner of Kingsway Financial Services Inc. (KFS), selling 55,000 shares of common stock on December 8–9, 2025. Stilwell Associates, L.P. sold 35,000 shares at $12.82 and 20,000 shares at $12.80, while still holding 666,904 common shares indirectly for his benefit. He also holds 162,500 shares directly and additional large indirect blocks through related partnerships.

The group also owns several series of convertible preferred stock with stated value $25 per share, convertible at 2.63158 common shares per preferred share. These positions correspond to 52,631 common shares from Class D Preferred and 88,421 and 16,842 common shares from Class C Preferred held through different entities, with mandatory redemption dates on May 7, 2032 and February 12, 2032. This structure concentrates significant economic exposure and voting potential in one shareholder group, though the reported sales reduce that exposure slightly.

The transactions may be viewed as a modest trimming of holdings in one affiliated fund rather than an exit, given the remaining multi‑million share indirect ownership. The specified conversion terms and redemption dates for the preferred stock define a clear timeframe, through 2032, over which these instruments can add to the common share float. Key items to watch are any continued common share sales by the Stilwell entities and any future changes in the size or terms of the preferred positions.

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

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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)
12/08/2025

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	12/08/2025		S(2)		35,000	D	$12.82	666,904	I	See footnote(3)
Common Stock	12/09/2025		S(2)		20,000	D	$12.8	646,904	I	See footnote(3)
Common Stock								3,550,382	I	See footnote(4)
Common Stock								457,181	I	See footnote(5)
Common Stock								590,410	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 8, 2025 Stilwell Associates, L.P. ("Associates") sold 35,000 shares at $12.82; and on December 9, 2025 Associates sold 20,000 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/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell	12/10/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC	12/10/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P.	12/10/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P.	12/10/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P.	12/10/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	12/10/2025
	** 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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** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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FAQ

What insider transaction did KFS disclose in this Form 4?

The filing reports that Stilwell Associates, L.P., affiliated with director and 10% owner Joseph Stilwell, sold a total of 55,000 shares of Kingsway Financial Services Inc. common stock in early December 2025.

How many Kingsway (KFS) shares were sold and at what prices?

On December 8, 2025, Stilwell Associates sold 35,000 shares at $12.82 per share, and on December 9, 2025 it sold 20,000 shares at $12.80 per share.

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

Joseph Stilwell is reported as a Director and 10% Owner of Kingsway Financial Services Inc., and he files jointly with several Stilwell investment partnerships.

How many KFS shares does Stilwell Associates report owning after the Form 4 trades?

After the reported sales, Stilwell Associates, L.P. reports 646,904 Kingsway common shares as indirectly beneficially owned, with ownership attributed to Joseph Stilwell through his role at Stilwell Value LLC.

What other Kingsway (KFS) common share positions are reported by Stilwell-related funds?

The filing lists indirect beneficial ownership of 3,550,382 common shares by Stilwell Activist Investments, L.P., 457,181 shares by Stilwell Activist Fund, L.P., and 590,410 shares by Stilwell Value Partners VII, L.P.

How do the Class C and Class D preferred shares in KFS convert into common stock?

Both Class C and Class D preferred stock have a stated value of $25 per share and are convertible at any time into Kingsway common stock at a rate of 2.63158 common shares per preferred share, subject to customary adjustments.

When must Kingsway redeem the reported preferred stock classes?

All outstanding Class D Preferred Stock shall be redeemed by the company on May 7, 2032, and all outstanding Class C Preferred Stock shall be redeemed on February 12, 2032.