Kingsway Financial (KFS) CFO adds shares via employee purchase plan

Rhea-AI Filing Summary

Kingsway Financial Services Inc. reported that its CFO and EVP, Kent A. Hansen, acquired additional common shares through the company’s employee share purchase plan. On 12/16/2025, he bought 122 shares of common stock at $12.82 per share in an open-market purchase coded as an acquisition. Following this transaction, he beneficially owns 136,472 common shares.

The shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan, which allows eligible employees to contribute up to 5% of adjusted salary, with a 100% company match after 12 months of employment, and those contributions are used to buy Kingsway shares on the open market. His total holdings include 8,370 restricted shares granted on December 15, 2022, 14,204 restricted shares granted on March 26, 2024, and 20,728 restricted shares granted on December 4, 2024.

Insider Trade Summary

Net Buyer: 122 shares ($1,564)

Net Buy 1 txn

Insider Hansen Kent A

Role CFO & EVP

Bought 122 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	122	$12.82	$2K

Holdings After Transaction: Common Stock — 136,472 shares (Direct)

Footnotes (1)

1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker. Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

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
Estimated average burden
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^*

Hansen Kent A

(Last) (First) (Middle)

10 S. RIVERSIDE PLAZA

SUITE 1520

(Street)

CHICAGO IL 60606

(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		10% Owner
X	Officer (give title below)		Other (specify below)
	CFO & EVP

3. Date of Earliest Transaction (Month/Day/Year)
12/16/2025

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	12/16/2025		P		122(1)	A	$12.82	136,472(2)	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

Explanation of Responses:

1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

2. Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

	/s/ Robert E. Buckner II, attorney-in-fact for Kent A. Hansen	12/17/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transaction did Kingsway Financial Services (KFS) report?

The CFO and EVP, Kent A. Hansen, reported buying 122 shares of Kingsway Financial Services Inc. common stock on 12/16/2025 at a price of $12.82 per share.

How many Kingsway Financial Services (KFS) shares does the CFO own after this transaction?

After the reported purchase, Kent A. Hansen beneficially owns 136,472 shares of Kingsway Financial Services Inc. common stock.

Under what plan were the new Kingsway Financial (KFS) shares acquired?

The 122 shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which uses employee and company matching contributions to buy Kingsway shares on the open market.

How does the Kingsway America Inc. ESPP work for employees?

Eligible employees may contribute up to 5% of adjusted salary each payroll period, and after 12 months of employment the company matches 100% of the employee’s contribution. Combined contributions are used to purchase Kingsway Financial Services Inc. shares on the open market.

What restricted stock grants are included in the CFO’s Kingsway (KFS) holdings?

His total includes 8,370 restricted shares granted on December 15, 2022, 14,204 restricted shares granted on March 26, 2024, and 20,728 restricted shares granted on December 4, 2024.

Is this Kingsway (KFS) Form 4 filed by a single reporting person?

Yes. The filing indicates it is a Form filed by one reporting person, covering transactions by Kent A. Hansen, the company’s CFO and EVP.