# EDGAR Filing Document

**Accession Number:** 0001071674
**File Stem:** 0001104659-25-123363
**Filing Date:** 2025-12
**Character Count:** 7728
**Document Hash:** 017031d96973a6eb34080a5d03dc495f
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001104659-25-123363.hdr.sgml**: 20251219

**ACCESSION NUMBER**: 0001104659-25-123363

**CONFORMED SUBMISSION TYPE**: 4

**PUBLIC DOCUMENT COUNT**: 1

**CONFORMED PERIOD OF REPORT**: 20251217

**FILED AS OF DATE**: 20251219

**DATE AS OF CHANGE**: 20251219

**REPORTING-OWNER**: 

**OWNER DATA:**
- **COMPANY CONFORMED NAME:** OAKMONT CAPITAL INC
- **CENTRAL INDEX KEY:** 0001071674

**ORGANIZATION NAME:**
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** 4
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-15204
- **FILM NUMBER:** 251588954

**BUSINESS ADDRESS:**
- **STREET 1:** 112 ST.CLAIR AVENUE WEST
- **STREET 2:** SUITE 400
- **CITY:** ONTARIO
- **STATE:** Z4
- **ZIP:** M4V 2Y3
- **BUSINESS PHONE:** 416-923-1477

**MAIL ADDRESS:**
- **STREET 1:** 112 ST.CLAIR AVENUE WEST
- **STREET 2:** SUITE 400
- **CITY:** ONTARIO
- **STATE:** Z4
- **ZIP:** M4V 2Y3
**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>OAKMONT CAPITAL INC<br><sub>(Last) (First) (Middle)</sub><br>45 ST. CLAIR AVENUE WEST<br>SUITE 400<br><sub>(Street)</sub><br>TORONTO ONTARIO, A6 M4V 1K9<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>[ ] Director [X] 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<sup>(1)</sup> |  | 500000 | D | 8.25<sup>(1)</sup> | 1987830 | D |  |

---

## 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 |
| Class B Preferred Stock | 9.50<sup>(2)</sup> |  |  |  |  |  |  | 2024-09-24 | 2031-09-24<sup>(2)</sup> | Common Stock | 210526.4<sup>(2)</sup> |  | 80000 | D |  |
| Class C Preferred Stock | 9.50<sup>(3)</sup> |  |  |  |  |  |  | 2025-02-12 | 2032-02-12<sup>(3)</sup> | Common Stock | 105263.2<sup>(3)</sup> |  | 40000 | D |  |
| Stock Option (obligation to sell) | $8.25 | 2025-12-17 |  | X<sup>(1)</sup> |  |  | 500000 | <sup>(1)</sup> | 2025-12-29<sup>(1)</sup> | Common Stock | 500000 | $0 | 0 | D |  |

---

### Footnotes:

(1) On March 31, 2025, Oakmont Capital Inc. ("Oakmont") entered into an Option Agreement with David Capital Partners Special Situation Fund, LP ("DCPSS"), pursuant to which Oakmont granted DCPSS an option to purchase 500,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company") at an exercise price of $8.25 per share. The Option Agreement was set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and was amended on December 17, 2025 so that the option became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.

(2) The shares of Class B 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 B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

(3) 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.

**Signature:** /s/ Kent Hansen, as attorney-in-fact for OAKMONT CAPITAL INC  
**Date:** 2025-12-19

### 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.**