Kingsway Financial Services Inc.

12/18/2025 | Press release | Distributed by Public on 12/18/2025 15:15

Statement of Changes in Beneficial Ownership (Form 4)

FORM 4
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 that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES 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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(Print or Type Responses)
1. Name and Address of Reporting Person *
Horowitz Joshua
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)
(Last) (First) (Middle)
C/O PALM MANAGEMENT (US) LLC, 19 WEST ELM STREET
3. Date of Earliest Transaction (Month/Day/Year)
12/17/2025
(Street)
GREENWICH, CT 06830
4. If Amendment, Date 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
(City) (State) (Zip)
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)
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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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 Underlying Securities
(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 of Derivative Security: 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 $9.50(1) 05/08/2025(1) 05/08/2032(1) Common Stock 36,842.40(1) 14,000 I Palm Global Small Cap Master Fund LP(2)

Reporting Owners

Reporting Owner Name / Address Relationships
Director 10% Owner Officer Other
Horowitz Joshua
C/O PALM MANAGEMENT (US) LLC
19 WEST ELM STREET
GREENWICH, CT 06830
X

Signatures

/s/ Joshua Horowitz 12/18/2025
**Signature of Reporting Person Date

Explanation of Responses:

* 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).
(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.
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure. Potential persons who are to respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB number.
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