[Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity

Rhea-AI Filing Summary

Oakmont Capital Inc., a 10% owner and director-level affiliate of Kingsway Financial Services Inc. (KFS), reported a transaction involving 500,000 shares of Kingsway common stock. On December 17, 2025, Oakmont entered into a stock option (an obligation to sell) covering 500,000 common shares at a price of $8.25 per share, pursuant to an Option Agreement with David Capital Partners Special Situation Fund, LP that is exercisable up to 5:00 p.m. Eastern Time on December 29, 2025. After this reported transaction, Oakmont directly beneficially owns 1,987,830 shares of common stock. Oakmont also holds Class B and Class C Preferred Stock that are each convertible into common stock at a rate of 2.63158 common shares per preferred share, with all Class B Preferred Stock subject to redemption on September 24, 2031 and all Class C Preferred Stock subject to redemption on February 12, 2032.

Insider Trade Summary

500,000 shares exercised/converted

Mixed 4 txns

Insider OAKMONT CAPITAL INC

Role 10% Owner

Type	Security	Shares	Price	Value
X	Stock Option (obligation to sell)	500,000	$0.00	--
X	Common Stock	500,000	$8.25	$4.13M
holding	Class B Preferred Stock	--	--	--
holding	Class C Preferred Stock	--	--	--

Holdings After Transaction: Stock Option (obligation to sell) — 0 shares (Direct); Common Stock — 1,987,830 shares (Direct); Class B Preferred Stock — 210,526.4 shares (Direct); Class C Preferred Stock — 105,263.2 shares (Direct)

Footnotes (1)

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. 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. 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.

Form 4 Insider Transactions: What Each Field Means →

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

OMB Number:			3235-0287
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hours per response:			0.5

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^*

OAKMONT CAPITAL INC

(Last) (First) (Middle)

45 ST. CLAIR AVENUE WEST

SUITE 400

(Street)

TORONTO ONTARIO 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)

	Director	X	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	D

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	D
Class C Preferred Stock	$9.5(3)							02/12/2025	02/12/2032(3)	Common Stock	105,263.2(3)		40,000	D
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	D

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 OAKMONT CAPITAL INC	12/19/2025
	** Signature of Reporting Person	Date
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