# EDGAR Filing Document

**Accession Number:** 0001612424
**File Stem:** 0001104659-25-122549
**Filing Date:** 2025-12
**Character Count:** 8040
**Document Hash:** d985d3d7a81d182ccf9f359cacefc3b0
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001104659-25-122549.hdr.sgml**: 20251218

**ACCESSION NUMBER**: 0001104659-25-122549

**CONFORMED SUBMISSION TYPE**: 4

**PUBLIC DOCUMENT COUNT**: 1

**CONFORMED PERIOD OF REPORT**: 20251217

**FILED AS OF DATE**: 20251218

**DATE AS OF CHANGE**: 20251218

**REPORTING-OWNER**: 

**OWNER DATA:**
- **COMPANY CONFORMED NAME:** Horowitz Joshua
- **CENTRAL INDEX KEY:** 0001612424

**ORGANIZATION NAME:**

**FILING VALUES:**
- **FORM TYPE:** 4
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-15204
- **FILM NUMBER:** 251583262

**MAIL ADDRESS:**
- **STREET 1:** 72-38 113TH STREET
- **STREET 2:** APARTMENT 3L
- **CITY:** FOREST HILLS
- **STATE:** NY
- **ZIP:** 11375
**ISSUER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** KINGSWAY FINANCIAL SERVICES INC
- **CENTRAL INDEX KEY:** 0001072627
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 999999999
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**BUSINESS ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606
- **BUSINESS PHONE:** (312) 766-2144

**MAIL ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606

### UNITED STATES SECURITIES AND EXCHANGE COMMISSION
**Washington, D.C. 20549**

## FORM 4

### STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

[ ] 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**<sup>*</sup><br>Horowitz Joshua<br><sub>(Last) (First) (Middle)</sub><br>C/O PALM MANAGEMENT (US) LLC<br>19 WEST ELM STREET<br><sub>(Street)</sub><br>GREENWICH, CT 06830<br><sub>(City) (State) (Zip)</sub> | **3. Date of Earliest Transaction (Month/Day/Year)**<br>2025-12-17 | **5. Relationship of Reporting Person(s) to Issuer**<br>(Check all applicable)<br>[X] Director [ ] 10% Owner<br>[ ] Officer (give title below) [ ] Other (specify below)<br>_ _ |
| **2. Issuer Name and Ticker or Trading Symbol**<br>KINGSWAY FINANCIAL SERVICES INC [ KFS ] | **4. If Amendment, Date of Original Filed (Month/Day/Year)**<br>  | **6. Individual or Joint/Group Filing (Check Applicable Line)**<br>[X] Form filed by One Reporting Person<br>[ ] Form filed by More than One Reporting Person |

---

## Table I - Non-Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | 3. Transaction Code (V) | 3. Transaction Code (V) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | Code | V | Amount | (A) or (D) | Price | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| Common Stock | 2025-12-17 |  | X |  | 22500 | A | $8.25 | 32500 | D |  |
| Common Stock | 2025-12-17 |  | X |  | 252500 | A | $8.25 | 367500 | I | by Palm Global Small Cap Master Fund LP<sup>(2)</sup> |

---

## Table II - Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | 4. Transaction Code (V) | 4. Transaction Code (V) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 6. Date Exercisable and Expiration Date | 6. Date Exercisable and Expiration Date | 7. Title and Amount of Underlying Securities | 7. Title and Amount of Underlying Securities | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | Code | V | (A) | (D) | Date Exercisable | Expiration Date | Title | Amount or Number of Shares | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| Stock Option (Right to Buy) | $8.25 | 2025-12-17 |  | X |  |  | 22500 | <sup>(3)</sup> | 2025-12-29<sup>(3)</sup> | Common Stock | 22500 | $0 | 0 | D |  |
| Stock Option (Right to Buy) | $8.25 | 2025-12-17 |  | X |  |  | 252500 | <sup>(3)</sup> | 2025-12-29<sup>(3)</sup> | Common Stock | 252500 | $0 | 0 | I | by Palm Global Small Cap Master Fund LP<sup>(2)</sup> |
| Class D Preferred Stock | 9.5<sup>(1)</sup> |  |  |  |  |  |  | 2025-05-08<sup>(1)</sup> | 2032-05-08<sup>(1)</sup> | Common Stock | 36842.4<sup>(1)</sup> |  | 14000 | I | Palm Global Small Cap Master Fund LP<sup>(2)</sup> |

---

### Footnotes:

(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.

**Signature:** /s/ Joshua Horowitz  
**Date:** 2025-12-18

### Remarks:

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.**