Kingsway Financial (KFS) director reports $8.25 common stock option exercises

Rhea-AI Filing Summary

Kingsway Financial Services Inc. director Joshua Horowitz reported exercising options on 12/17/2025 to acquire 22,500 shares of common stock at $8.25 per share, increasing his direct holdings to 32,500 common shares.

On the same date, Palm Global Small Cap Master Fund LP acquired 252,500 common shares at $8.25, resulting in 367,500 common shares reported as indirectly owned, with Palm Management (US) LLC and Mr. Horowitz stating they may be deemed beneficial owners through Palm Global but expressly disclaiming beneficial ownership beyond their pecuniary interest. Palm Global also holds 14,000 shares of Class D Preferred Stock, each with a stated value of $25 and initially convertible into 2.6316 common shares at a conversion price of $9.50 per share, with all then-outstanding Class D Preferred Stock to be redeemed for cash on May 8, 2032.

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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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^*

Horowitz Joshua

(Last) (First) (Middle)

C/O PALM MANAGEMENT (US) LLC

19 WEST ELM STREET

(Street)

GREENWICH CT 06830

(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		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
12/17/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	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	12/17/2025		X		22,500	A	$8.25	32,500	D
Common Stock	12/17/2025		X		252,500	A	$8.25	367,500	I	by Palm Global Small Cap Master Fund LP(2)

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
Stock Option (Right to Buy)	$8.25	12/17/2025		X			22,500	(3)	12/29/2025(3)	Common Stock	22,500	$0	0	D
Stock Option (Right to Buy)	$8.25	12/17/2025		X			252,500	(3)	12/29/2025(3)	Common Stock	252,500	$0	0	I	by Palm Global Small Cap Master Fund LP(2)
Class D Preferred Stock	$9.5(1)							05/08/2025(1)	05/08/2032(1)	Common Stock	36,842.4(1)		14,000	I	Palm Global Small Cap Master Fund LP(2)

Explanation of Responses:

1. The shares of Class D Preferred Stock, par value $0.01 per share (the "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, at the holder's option, into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at an initial conversion price of $9.50 per share (or 2.6316 shares of Common Stock for each share of Class D Preferred Stock), subject to customary adjustments. The Company has the option to redeem 25% of the outstanding shares of Class D Preferred Stock for cash upon the occurrence of certain events. All then-outstanding shares of Class D Preferred Stock shall be redeemed by the Company for cash on May 8, 2032.

2. Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

3. On March 31, 2025, Mr. Horowitz and Palm Global entered into an option agreement with Stilwell Value LLC, (the "Option Agreement") to acquire 22,500 and 252,500 shares of Common Stock, respectively, at an exercise price of $8.25 per share, which Option Agreement was amended on December 17, 2025, to allow for the early exercise of the options. The options had an expiration of December 29, 2025 at 5:00 p.m. Eastern Time.

	/s/ Joshua Horowitz	12/18/2025
	** 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 did Kingsway Financial (KFS) director Joshua Horowitz report?

Director Joshua Horowitz reported exercising options on 12/17/2025 to acquire 22,500 shares of Kingsway Financial common stock at $8.25 per share. The exercise increased his directly held common stock to 32,500 shares.

How many Kingsway Financial (KFS) shares does Joshua Horowitz hold after the reported transactions?

After the reported transactions, Joshua Horowitz holds 32,500 shares of Kingsway Financial common stock directly. The filing also reports 367,500 common shares as indirectly owned through Palm Global Small Cap Master Fund LP, for which Palm Management (US) LLC and Mr. Horowitz may be deemed beneficial owners but expressly disclaim beneficial ownership except to the extent of their pecuniary interest.

What were the terms of the option agreement described in the Kingsway Financial (KFS) Form 4?

On March 31, 2025, Mr. Horowitz and Palm Global Small Cap Master Fund LP entered into an option agreement with Stilwell Value LLC to acquire 22,500 and 252,500 shares of Kingsway Financial common stock, respectively, at an exercise price of $8.25 per share. The agreement was amended on December 17, 2025 to allow early exercise, and the options had an expiration of December 29, 2025 at 5:00 p.m. Eastern Time.

What is Kingsway Financial (KFS) Class D Preferred Stock and how is it convertible?

The Class D Preferred Stock of Kingsway Financial has a stated value of $25 per share and is convertible at any time, at the holder's option, into common stock at an initial conversion price of $9.50 per share. This equals 2.6316 shares of common stock for each share of Class D Preferred Stock, subject to customary adjustments.

What indirect holdings in Kingsway Financial (KFS) does Palm Global Small Cap Master Fund LP report?

Palm Global Small Cap Master Fund LP is reported as holding 367,500 shares of Kingsway Financial common stock indirectly for Mr. Horowitz after exercising options to acquire 252,500 shares at $8.25 per share. It also holds 14,000 shares of Class D Preferred Stock, which are initially convertible into 36,842.4 shares of common stock, with Palm Management (US) LLC and Mr. Horowitz stating they may be deemed beneficial owners but expressly disclaiming beneficial ownership beyond their pecuniary interest.

When will Kingsway Financial (KFS) Class D Preferred Stock be redeemed for cash?

The Company has the option to redeem 25% of the outstanding shares of Class D Preferred Stock for cash upon the occurrence of certain events, and all then-outstanding shares of Class D Preferred Stock shall be redeemed by the Company for cash on May 8, 2032.