[Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity

Rhea-AI Filing Summary

Joseph Stilwell and affiliated entities reported insider sales of Kingsway Financial Services Inc. (KFS) common stock on September 16-17, 2025. The Form 4 shows aggregate sales by three affiliated investment vehicles of 68,000 common shares: 20,000 shares sold on 09/16/2025 at $14.40 and 48,000 shares sold on 09/17/2025 at $14.47. After these transactions certain indirect holdings remain large, with the largest reported indirect position totaling 3,550,382 shares following the 09/17 trades and other indirect holdings reported at 457,181, 590,410 and 701,904 through affiliated entities. The filing also discloses convertible Class C and Class D preferred stakes that convert into common shares (conversion rate 2.63158) and remaining derivative common equivalents reported as 52,631 and 88,421/16,842 across certain preferred positions. The Form 4 is signed by an attorney-in-fact on behalf of Stilwell and his affiliated entities.

Positive

• Full Section 16 disclosure provided with specific transaction dates, prices, and amounts, meeting regulatory transparency requirements
• Substantial retained indirect holdings after the trades (e.g., 3,550,382 shares reported indirect), indicating continued significant economic interest
• Convertible preferred terms disclosed (conversion rate 2.63158 and redemption dates), clarifying potential future common share exposure

Negative

• Insider dispositions of 68,000 common shares over two days (20,000 at $14.40 and 48,000 at $14.47), which reduce affiliated holdings
• Potential dilution from convertible Class C and D preferred that convert into common stock at 2.63158 shares per preferred, adding contingent common exposure

Insights

Securities Analyst

TL;DR: Affiliates of Joseph Stilwell sold 68,000 KFS shares over two days but retain substantial indirect holdings and convertible preferred exposure.

These reported sales total 68,000 common shares: 20,000 on 09/16/2025 at $14.40 and 48,000 on 09/17/2025 at $14.47. The filing clarifies ownership chains: Stilwell holds interests indirectly via multiple funds and partnerships and disclaims direct beneficial ownership except to his pecuniary interest. Material indirect common positions remain, notably 3,550,382 shares after the 09/17 trades. The disclosure of convertible Class C and D preferred stock and their common equivalents (using a 2.63158 conversion factor) indicates additional potential common share exposure from preferred conversions and redemptions scheduled in 2032. The filing is a routine Section 16 report documenting dispositions and existing derivative exposure.

Corporate Governance Expert

TL;DR: The Form 4 documents insider dispositions via affiliated funds while preserving transparency about ownership structure and conversion features.

The report identifies Joseph Stilwell as a director and >10% owner and details that sales were executed by affiliated entities (SAI, SAF, SVP VII) with amounts and prices disclosed. It also provides clear explanatory footnotes about indirect ownership and disclaimers, and specifies convertible preferred terms (stated value $25; conversion 2.63158; redemption dates in 2032), which are important for assessing dilution. From a governance standpoint, the filing meets Section 16 disclosure requirements and clarifies the chain of ownership and the nature of the transactions.

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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OMB Number:			3235-0287
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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).

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)
09/16/2025

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	09/16/2025		S(2)		11,941	D	$14.4	3,579,039	I	See footnote(3)
Common Stock	09/16/2025		S(2)		2,106	D	$14.4	462,236	I	See footnote(4)
Common Stock	09/16/2025		S(2)		5,953	D	$14.4	604,698	I	See footnote(5)
Common Stock	09/17/2025		S(2)		28,657	D	$14.47	3,550,382	I	See footnote(3)
Common Stock	09/17/2025		S(2)		5,055	D	$14.47	457,181	I	See footnote(4)
Common Stock	09/17/2025		S(2)		14,288	D	$14.47	590,410	I	See footnote(5)
Common Stock								701,904	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(6)
Class C Preferred Stock	$9.5(8)							02/12/2025	02/12/2032(8)	Common Stock	88,421(8)		33,600	I	See footnote(3)
Class C Preferred Stock	$9.5(8)							02/12/2025	02/12/2032(8)	Common Stock	16,842(8)		6,400	I	See footnote(4)

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 September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

3. These are shares owned directly by 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.

4. These are shares owned directly by 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.

5. These are shares owned directly by 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.

6. 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.

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	09/18/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC	09/18/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P.	09/18/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P.	09/18/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P.	09/18/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	09/18/2025
	** 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.
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FAQ

What insider transactions did Joseph Stilwell report for KFS on this Form 4?

Affiliated entities sold a total of 68,000 common shares: 20,000 on 09/16/2025 at $14.40 and 48,000 on 09/17/2025 at $14.47.

How many KFS shares does Stilwell or his affiliates still indirectly own after these trades?

The filing reports an indirect position of 3,550,382 shares following the 09/17 transactions, plus other indirect holdings of 457,181, 590,410, and 701,904 across affiliated entities.

Are there any derivative or preferred holdings disclosed by the reporting persons?

Yes. The filing discloses Class D and Class C preferred stock convertible into common stock at a 2.63158 conversion rate, with reported common equivalents such as 52,631 and 88,421 common-share equivalents tied to those preferred positions.

When are the convertible preferred redemptions scheduled according to the filing?

The filing states Class D preferred are redeemable on May 7, 2032 and Class C preferred are redeemable on February 12, 2032.

Who signed the Form 4 on behalf of Joseph Stilwell and affiliates?

The Form 4 was signed by Debra Rouse as Attorney-in-Fact for Joseph Stilwell and the affiliated reporting entities, dated 09/18/2025.