[Form 4] Kingsway Financial Services, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Kingsway Financial Services, Inc. (KFS) Form 4 summary: Joseph Stilwell and affiliated entities reported multiple sales of KFS common stock on 08/22/2025. Stilwell Activist Investments, L.P. sold 44,772 shares, Stilwell Activist Fund, L.P. sold 7,642 shares, and Stilwell Value Partners VII, L.P. sold 22,586 shares, each at $14.1784 per share. After the reported transactions, the reporting parties hold significant common stock positions: Joseph Stilwell directly holds 162,500 shares and beneficially holds additional shares through affiliated entities for totals shown on the form. The filing also discloses ownership of Class C and Class D preferred shares convertible into common stock at 2.63158 shares per preferred share, with redemption dates in 2032. The Form 4 is signed by Debra Rouse as attorney-in-fact for the reporting persons.

Positive

• Transparent attribution: Sales are clearly attributed to specific affiliated entities with explanatory footnotes.
• Retention of material holdings: Reporting persons continue to hold substantial direct and indirect common stock and convertible preferred shares, preserving influence.

Negative

• Insider selling: Affiliated funds sold common shares on 08/22/2025, reducing the group's holdings by reported amounts.
• Potential liquidity event: Multiple simultaneous sales by affiliated entities may be interpreted as coordinated dispositions.

Insights

Securities Analyst

TL;DR: Insider and affiliated entities sold a modest block of common shares at $14.1784, while retaining sizable direct and indirect holdings and convertible preferred interests.

The transactions on 08/22/2025 show targeted dispositions by three affiliated funds totaling 74, ("74,000") shares sold across entities at $14.1784 per share according to the Form 4 line items: 44,772; 7,642; and 22,586. The reporting group continues to report material beneficial ownership through direct holdings and multiple affiliated partnerships, plus convertible Class C and Class D preferred stock convertible at 2.63158x into common stock and redeemable in 2032. These disclosures reflect liquidity actions rather than complete exits and maintain continued influence through retained positions and convertible securities.

Corporate Governance Expert

TL;DR: Multiple affiliated filers executed sales but retain control-linked positions; disclosure includes conversion mechanics for preferred stock.

The Form 4 identifies Joseph Stilwell as a director and 10% owner and lists multiple affiliated entities as reporting persons. Sales by Stilwell-managed funds were executed on the same date and price, and the filing discloses indirect ownership via a general partner structure with customary disclaimers of beneficial ownership except for pecuniary interest. The presence of convertible Class C and D preferred stock, with explicit conversion ratios and 2032 redemption dates, is material to voting and economic exposure. The filing is procedural and transparent in attribution and signatures.

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
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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)
08/22/2025

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	08/22/2025		S(2)		44,772	D	$14.1784	3,605,924	I	See footnote(3)
Common Stock	08/22/2025		S(2)		7,642	D	$14.1784	466,893	I	See footnote(4)
Common Stock	08/22/2025		S(2)		22,586	D	$14.1784	618,156	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 August 22, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 44,772 shares at $14.1784; (b) Stilwell Activist Fund, L.P. ("SAF") sold 7,642 shares at $14.1784; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 22,586 shares at $14.1784.

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	08/26/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC	08/26/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P.	08/26/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P.	08/26/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P.	08/26/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	08/26/2025
	** 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.

FAQ

What shares were sold by insiders of KFS on 08/22/2025?

Stilwell Activist Investments, L.P. sold 44,772 shares, Stilwell Activist Fund, L.P. sold 7,642 shares, and Stilwell Value Partners VII, L.P. sold 22,586 shares at $14.1784 per share.

How many shares does Joseph Stilwell directly own according to the Form 4?

Joseph Stilwell directly owns 162,500 shares as reported on the Form 4.

Are there preferred securities disclosed and how do they convert?

Yes. Class C and Class D preferred shares convert into common stock at 2.63158 common shares per preferred share; redemption dates are in 2032.

Who signed the Form 4 for the reporting persons?

Debra Rouse signed as attorney-in-fact for Joseph Stilwell and each affiliated reporting entity on 08/26/2025.

Does the filing indicate Joseph Stilwell retains indirect ownership through affiliates?

Yes. Footnotes state that several entities own shares directly and Joseph Stilwell is indirect beneficial owner via his role with Stilwell Value LLC, with a disclaimer except to his pecuniary interest.