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

Rhea-AI Filing Summary

Kingsway Financial Services, Inc. insider filing reports multiple August 18, 2025 sales by entities affiliated with Joseph Stilwell while retaining substantial ownership. The Form 4 shows aggregated dispositions of 71,429 common shares across Stilwell Activist Investments, L.P., Stilwell Activist Fund, L.P., and Stilwell Value Partners VII, L.P., at prices between $13.95 and $14.1631. After the transactions, certain affiliated entities and Mr. Stilwell continue to beneficially own large positions, including reported indirect holdings of 3,650,696, 701,904 (derivative-convertible basis noted), and other specified share counts. The filing also discloses convertible Class C and D preferred stakes convertible into common shares.

Positive

• Transparent disclosure of all transactions and indirect ownership structures by affiliated entities and Mr. Stilwell
• Significant retained ownership: multiple entities continue to hold multi-million-share positions after the sales
• Convertible preferred details provided including conversion ratio (2.63158) and redemption dates for Class C and D preferred

Negative

• Insider dispositions totaling 71,429 common shares on 08/18/2025 executed at $13.95 and $14.1631
• Sales by multiple affiliated funds may be interpreted by some investors as liquidity-taking by insiders (no rationale disclosed in filing)

Insights

Financial Analyst

TL;DR: Insider-affiliated entities sold 71,429 KFS shares on August 18, 2025 at roughly $13.95–$14.16, yet retain multi-million-share positions.

The transactions are outright sales reported on Form 4 by affiliated funds controlled by Joseph Stilwell. Total disclosed common share dispositions equal 71,429 shares executed at two price points. The filing also details existing indirect common stock holdings across entities and convertible preferred securities that convert at 2.63158 common shares per preferred. From a capital-structure view, these are liquidity actions by insiders while significant ownership is preserved; the filing contains no information about reasons for the sales or company operational metrics.

Corporate Governance Expert

TL;DR: Multiple affiliated reporting persons executed sales but retain substantial beneficial ownership and disclose conversion features of preferred shares.

The Form 4 properly discloses the sales by Stilwell-affiliated entities and the indirect ownership chain (Value as general partner). It also provides conversion details for Class C and D preferred shares and redemption dates. All reported ownership is accompanied by disclaimers of beneficial ownership except for pecuniary interest. The filing is procedural and transparent; it does not allege any governance actions or changes to board composition.

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)
08/18/2025

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	08/18/2025		S(2)		23,779	D	$13.95	3,669,531	I	See footnote(3)
Common Stock	08/18/2025		S(2)		4,098	D	$13.95	477,719	I	See footnote(4)
Common Stock	08/18/2025		S(2)		12,123	D	$13.95	650,152	I	See footnote(5)
Common Stock	08/18/2025		S(2)		18,835	D	$14.1631	3,650,696	I	See footnote(3)
Common Stock	08/18/2025		S(2)		3,184	D	$14.1631	474,535	I	See footnote(4)
Common Stock	08/18/2025		S(2)		9,410	D	$14.1631	640,742	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 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

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	08/20/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC	08/20/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P.	08/20/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P.	08/20/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P.	08/20/2025
	/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P.	08/20/2025
	** 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 in the KFS Form 4?

Affiliated entities sold a combined 71,429 common shares on 08/18/2025 across transactions at prices of $13.95 and $14.1631.

How many KFS shares do Stilwell-affiliated entities still beneficially own after the transactions?

The filing reports indirect/common holdings including 3,650,696 and additional holdings such as 701,904 shares (including shares underlying convertible preferred interests).

Are there convertible securities disclosed in the KFS Form 4?

Yes. The filing discloses Class C and Class D preferred stock convertible at 2.63158 common shares per preferred share with specified redemption dates in 2032.

Who filed the Form 4 for KFS and who signed it?

The reporting persons are Joseph Stilwell and several Stilwell-affiliated entities; the form is signed by Debra Rouse as Attorney-in-Fact for each reporting person on 08/20/2025.

Does the Form 4 explain why the shares were sold?

No. The filing lists the sales, prices, and amounts but does not provide any explanation or business rationale for the dispositions.