Kingsway (KFS) CFO Acquires Shares via ESPP, Holdings Now 135,791

Rhea-AI Filing Summary

Kent A. Hansen, Chief Financial Officer and Executive Vice President of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan on 09/15/2025. The filing shows a purchase (code P) at $14.36 per share for 109 shares acquired through the ESPP administrator. Following the transaction, Mr. Hansen beneficially owns 135,791 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares from 2022, March 2024 and December 2024 respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of service; shares are purchased on the open market by the plan administrator.

Positive

• Insider participation via the ESPP (purchase at $14.36) demonstrates continued executive ownership and alignment with shareholders
• Clear disclosure of restricted stock holdings (8,370; 14,204; 20,728) provides transparency about compensation-related equity

Negative

• None.

Insights

Financial Analyst

TL;DR: Insider participation via the ESPP shows modest personal purchase and continued equity exposure, a small positive governance signal.

The transaction is a routine purchase through the company's ESPP at $14.36 per share for 109 shares, increasing the reporting person's stake to 135,791 shares. This filing reflects compensation and retention mechanisms rather than open-market opportunistic buying by an executive. The inclusion of multiple restricted stock grants indicates ongoing equity-based compensation. For investors, the purchase size is immaterial to capital structure but signals continued alignment with shareholders through participation in the ESPP.

Corporate Governance Expert

TL;DR: Purchase via ESPP and presence of recent restricted grants are standard governance practices; no material change to control.

The Form 4 discloses an ESPP purchase and notes prior restricted stock awards. The plan's 100% match after 12 months and open-market acquisition by the plan administrator are compliant with common corporate compensation policies. There is no indication of unusual timing, related-party arrangements, or material shifts in beneficial ownership that would raise governance concerns. The filing is routine and transparent.

Insider Trade Summary

Net Buyer: 109 shares ($1,565)

Net Buy 1 txn

Insider Hansen Kent A

Role CFO & EVP

Bought 109 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	109	$14.36	$2K

Holdings After Transaction: Common Stock — 135,791 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)
09/15/2025

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	09/15/2025		P		109(1)	A	$14.36	135,791(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/ Debra Rouse, attorney-in-fact for Kent A. Hansen	09/16/2025
	** 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 did Kent A. Hansen report on Form 4 for KFS?

He reported a purchase of 109 shares under the ESPP on 09/15/2025 at $14.36 per share and now beneficially owns 135,791 shares.

How were the shares purchased by the reporting person acquired?

The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan (ESPP), with the plan administrator buying shares on the open market via a broker.

What equity compensation does the filing disclose for Kent A. Hansen?

The filing states he holds restricted stock grants of 8,370, 14,204, and 20,728 shares granted on December 15, 2022; March 26, 2024; and December 4, 2024, respectively.

What are key ESPP terms disclosed in the Form 4?

Eligible employees may contribute up to 5% of adjusted salary; after 12 months of employment the company matches 100% of the employee contribution, used to purchase company shares.

Does the Form 4 indicate any sale or other disposition by the reporting person?

No. The filing records a purchase (code P); there is no sale or disposition reported in this Form 4.