Kingsway Financial Services Inc. (KFS) director logs 500,000-share option at $8.25

Rhea-AI Filing Summary

Oakmont Capital Inc., a director of Kingsway Financial Services Inc. (KFS), reported a significant change in its holdings of the company’s common stock. On December 17, 2025, Oakmont disposed of 500,000 shares of common stock at $8.25 per share through a stock option arrangement and reported indirect ownership of 1,987,830 common shares afterward, held through Oakmont.

Oakmont also reports additional indirect holdings of common stock through a retirement plan, spouse, and a trust. Beyond common shares, Oakmont holds Class B Preferred Stock with a stated value of $25 per share, convertible into 2.63158 common shares per preferred share and redeemable on September 24, 2031, and Class C Preferred Stock with the same conversion terms, redeemable on February 12, 2032.

The transaction stems from an option agreement with David Capital Partners Special Situation Fund, LP, originally dated March 31, 2025 and amended on December 17, 2025 so the option to purchase the 500,000 common shares at $8.25 can be exercised at any time before 5:00 p.m. Eastern Time on December 29, 2025.

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

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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^*

Hannon Gregory Paul

(Last) (First) (Middle)

OAKMONT CAPITAL INC.

45 ST. CLAIR AVENUE WEST, SUITE 400

(Street)

TORONTO A6 M4V 1K9

(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(1)		500,000	D	$8.25(1)	1,987,830	I	By Oakmont Capital Inc
Common Stock								29,500	I	By Retirement Plan (R)
Common Stock								13,750	I	By Spouse
Common Stock								4,500	I	By Trust

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 B Preferred Stock	$9.5(2)							09/24/2024	09/24/2031(2)	Common Stock	210,526.4(2)		80,000	I	By Oakmont Capital Inc.
Class C Preferred Stock	$9.5(3)							02/12/2025	02/12/2032(3)	Common Stock	105,263.2(3)		40,000	I	By Oakmont Capital Inc.
Stock Option (obligation to sell)	$8.25	12/17/2025		X(1)			500,000	(1)	12/29/2025(1)	Common Stock	500,000	$0	0	I	By Oakmont Capital Inc.

Explanation of Responses:

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.

	/s/ Kent Hansen, as attorney-in-fact for Gregory Paul Hannon	12/19/2025
	** Signature of Reporting Person	Date
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FAQ

What insider transaction did Oakmont Capital Inc. report for Kingsway Financial Services Inc. (KFS)?

Oakmont Capital Inc., a director of Kingsway Financial Services Inc., reported disposing of 500,000 shares of common stock at $8.25 per share on December 17, 2025, in connection with a stock option arrangement.

How many Kingsway (KFS) shares does Oakmont Capital Inc. report owning after the transaction?

Following the reported transaction, Oakmont Capital Inc. reports indirect beneficial ownership of 1,987,830 shares of Kingsway common stock through Oakmont, plus additional indirect holdings via a retirement plan, spouse, and a trust.

What are the key terms of the 500,000-share option involving Oakmont Capital and David Capital Partners?

On March 31, 2025, Oakmont granted David Capital Partners Special Situation Fund, LP an option to purchase 500,000 shares of Kingsway common stock at an exercise price of $8.25 per share. The option expires at 5:00 p.m. Eastern Time on December 29, 2025 and was amended on December 17, 2025 so it can be exercised at any time before that expiration.

What are the conversion terms of Kingsway’s Class B Preferred Stock held by Oakmont Capital Inc.?

The Class B Preferred Stock has a stated value of $25 per share and is convertible at any time into Kingsway common stock at a rate of 2.63158 common shares for each preferred share, subject to customary adjustments. All outstanding Class B Preferred shares are to be redeemed on September 24, 2031.

What are the conversion terms of Kingsway’s Class C Preferred Stock held by Oakmont Capital Inc.?

The Class C Preferred Stock also has a stated value of $25 per share and is convertible at any time into Kingsway common stock at 2.63158 common shares for each preferred share, subject to customary adjustments. All outstanding Class C Preferred shares are to be redeemed on February 12, 2032.

What is Oakmont Capital Inc.’s relationship to Kingsway Financial Services Inc. (KFS)?

Oakmont Capital Inc. is identified as a director of Kingsway Financial Services Inc., making this a reporting person transaction for Form 4 purposes.