Terence Michael Kavanagh - 17 Dec 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: Director
Signature: /s/ Kent Hansen, as attorney-in-fact for Terence Michael Kavanagh
Issuer symbol: KFS
Transactions as of: 17 Dec 2025
Transactions value $: -$4,125,000
Form type: 4
Filing time: 19 Dec 2025, 19:14:33 UTC
Previous filing: 14 Feb 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Kavanagh Terence Michael	Director	OAKMONT CAPITAL INC., 45 ST. CLAIR AVENUE WEST, SUITE 400, TORONTO, ONTARIO, CANADA	/s/ Kent Hansen, as attorney-in-fact for Terence Michael Kavanagh	19 Dec 2025	0001538185

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	KFS	Common Stock	Exercise of in-the-money or at-the-money derivative security	-$4.13M	-500K	-20.1%	$8.25	1.99M	17 Dec 2025	By Oakmont Capital Inc.	F1
holding	KFS	Common Stock						34.8K	17 Dec 2025	By Retirement Plan

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	KFS	Stock Option (obligation to sell)	Exercise of in-the-money or at-the-money derivative security	$0	-500K	-100%	$0.00	0	17 Dec 2025	Common Stock	500K	$8.25	By Oakmont Capital Inc.	F1
holding	KFS	Class B Preferred Stock						80K	17 Dec 2025	Common Stock	211K	$9.50	By Oakmont Capital Inc.	F2
holding	KFS	Class C Preferred Stock						40K	17 Dec 2025	Common Stock	105K	$9.50	By Oakmont Capital Inc.	F3

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.
F2	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.
F3	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.