Joseph Stilwell - Feb 12, 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: Director, 10%+ Owner
Signature: /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell
Stock symbol: KFS
Transactions as of: Feb 12, 2025
Transactions value $: $1,000,000
Form type: 4
Date filed: 2/14/2025, 05:16 PM
Previous filing: Jan 3, 2025
Next filing: Feb 26, 2025
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
holding	KFS	Common Stock						163K	Feb 12, 2025	Direct	F1
holding	KFS	Common Stock						4.31M	Feb 12, 2025	See footnote	F2
holding	KFS	Common Stock						568K	Feb 12, 2025	See footnote	F3
holding	KFS	Common Stock						919K	Feb 12, 2025	See footnote	F4
holding	KFS	Common Stock						905K	Feb 12, 2025	See footnote	F5

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	Class C Preferred Stock	Award	$840K	+33.6K		$25.00	33.6K	Feb 12, 2025	Common Stock	88.4K	$9.50	See footnote	F2, F6
transaction	KFS	Class C Preferred Stock	Award	$160K	+6.4K		$25.00	6.4K	Feb 12, 2025	Common Stock	16.8K	$9.50	See footnote	F3, F6

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

Explanation of Responses:

Id	Content
F1	These are shares owned directly by Joseph Stilwell.
F2	These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F3	These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F4	These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F5	These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F6	The shares of Class C Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "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.