Joshua Horowitz - 17 Dec 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: Director
Signature: /s/ Joshua Horowitz
Issuer symbol: KFS
Transactions as of: 17 Dec 2025
Transactions value $: $2,268,750
Form type: 4
Filing time: 18 Dec 2025, 16:15:19 UTC
Previous filing: 12 Dec 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Horowitz Joshua	Director	C/O PALM MANAGEMENT (US) LLC, 19 WEST ELM STREET, GREENWICH	/s/ Joshua Horowitz	18 Dec 2025	0001612424

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	$186K	+22.5K	+225%	$8.25	32.5K	17 Dec 2025	Direct
transaction	KFS	Common Stock	Exercise of in-the-money or at-the-money derivative security	$2.08M	+253K	+219.57%	$8.25	368K	17 Dec 2025	by Palm Global Small Cap Master Fund LP	F2

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 (Right to Buy)	Exercise of in-the-money or at-the-money derivative security	$0	-22.5K	-100%	$0.00	0	17 Dec 2025	Common Stock	22.5K	$8.25	Direct	F3
transaction	KFS	Stock Option (Right to Buy)	Exercise of in-the-money or at-the-money derivative security	$0	-253K	-100%	$0.00	0	17 Dec 2025	Common Stock	253K	$8.25	by Palm Global Small Cap Master Fund LP	F2, F3
holding	KFS	Class D Preferred Stock						14K	17 Dec 2025	Common Stock	36.8K	$9.50	Palm Global Small Cap Master Fund LP	F1, F2

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

Explanation of Responses:

Id	Content
F1	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.
F2	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.
F3	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.