Kingsway (KFS) CFO & EVP increases stake through ESPP purchase

Rhea-AI Filing Summary

Kingsway Financial Services Inc. (KFS) filed a Form 4 reporting a routine employee share purchase by its CFO and EVP, Kent A. Hansen. On 11/17/2025, he acquired 123 shares of common stock at a price of $12.7 per share through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Following this transaction, he beneficially owned 136,230 common shares.

The ESPP allows eligible employees to contribute up to 5% of adjusted salary each pay period, with Kingsway America Inc. matching 100% of contributions for employees with at least 12 months of service, with all contributions used to buy Kingsway Financial Services Inc. shares on the open market. Hansen’s 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: 123 shares ($1,562)

Net Buy 1 txn

Insider Hansen Kent A

Role CFO & EVP

Bought 123 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	123	$12.70	$2K

Holdings After Transaction: Common Stock — 136,230 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)
11/17/2025

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	11/17/2025		P		123(1)	A	$12.7	136,230(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	11/19/2025
	** 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 KFS report on this Form 4?

The company reported that its CFO and EVP, Kent A. Hansen, acquired 123 shares of Kingsway Financial Services Inc. common stock on 11/17/2025 at a price of $12.7 per share through the employee share purchase plan.

How many KFS shares does the reporting person beneficially own after the transaction?

After the reported purchase, Kent A. Hansen beneficially owned 136,230 shares of Kingsway Financial Services Inc. common stock.

What is the Kingsway America Inc. Employee Share Purchase Plan (ESPP)?

Under the ESPP, eligible employees may contribute up to 5% of adjusted salary each regular payroll period, and if employed for at least 12 months, the company makes a 100% matching contribution. These contributions are used to purchase Kingsway Financial Services Inc. shares on the open market.

How are KFS shares acquired under the ESPP?

Employee and company matching contributions under the ESPP are used to buy Kingsway Financial Services Inc. shares on the open market, with purchases made by the ESPP administrator through a duly registered stockbroker.

What restricted stock grants are included in the reporting person’s KFS holdings?

The beneficial ownership 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.

What is the reporting person’s role and relationship to KFS?

The reporting person, Kent A. Hansen, is an officer of Kingsway Financial Services Inc., serving as CFO & EVP, and the Form 4 is filed for one reporting person.