Kingsway (KFS) CFO adds common shares through employee purchase plan

Rhea-AI Filing Summary

KINGSWAY FINANCIAL SERVICES INC executive Kent A. Hansen, the company’s CFO and EVP, made an open-market purchase of 143 shares of common stock at $10.93 per share on April 30, 2026. The shares were acquired through the company’s Employee Share Purchase Plan, which matches eligible employee contributions.

Following this transaction, Hansen directly holds 135,103 common shares, a figure that includes 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.

Insider Trade Summary

Net Buyer: 143 shares ($1,563)

Net Buy 1 txn

Insider Hansen Kent A

Role CFO & EVP

Bought 143 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	143	$10.93	$2K

Holdings After Transaction: Common Stock — 135,103 shares (Direct, null)

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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

Key Figures

Shares purchased: 143 shares Purchase price: $10.93 per share Shares held after transaction: 135,103 shares +3 more

6 metrics

Shares purchased 143 shares Open-market purchase on April 30, 2026

Purchase price $10.93 per share Common stock transaction on April 30, 2026

Shares held after transaction 135,103 shares Direct common stock holdings following purchase

Restricted stock grant 2024 6,909 shares Restricted stock granted on December 4, 2024

Restricted stock grant 2026 14,568 shares Restricted stock granted on March 17, 2026

Net shares bought 143 shares Net-buy direction in transaction summary

Key Terms

Employee Share Purchase Plan, restricted stock, open market, matching contribution

4 terms

Employee Share Purchase Plan financial

"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"

A program that lets employees buy their employer’s stock, often through regular payroll deductions and sometimes at a discounted price or with matching contributions; think of it as a company-run savings plan that converts part of pay into ownership. It matters to investors because it can increase insider ownership and employee motivation, potentially affecting company performance, and can slightly change share supply when new stock is issued or sold.

restricted stock financial

"Includes 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

open market financial

"The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker"

An open market is a system where buying and selling of goods, services, or financial assets happen freely without restrictions or special controls. For investors, it means they can trade assets easily and quickly, which helps determine fair prices based on supply and demand. This environment encourages transparency and competition, making it easier to buy or sell with confidence.

matching contribution financial

"the company will make a matching contribution equal to 100% of such employee's contribution"

An employer’s matching contribution is when a company adds money to an employee’s retirement or savings account based on the employee’s own contributions, like a store offering to top up a customer’s purchase to reach a discount threshold. It matters to investors because matching increases a firm’s compensation costs and can improve staff retention and morale, which affect productivity, cash flow and long-term liabilities that influence a company’s financial outlook.

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 ILLINOIS 60606

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
04/30/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	04/30/2026		P		143(1)	A	$10.93	135,103(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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

	/s/Debra S. Rouse, attorney-in-fact for Kent A. Hansen	05/04/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What did KFS CFO Kent Hansen do in this Form 4 filing?

KFS CFO Kent A. Hansen bought 143 shares of common stock at $10.93 per share. The purchase was executed through Kingsway’s Employee Share Purchase Plan, which uses employee and company matching contributions to acquire shares on the open market.

How many KFS shares does Kent Hansen own after this transaction?

After the transaction, Kent Hansen directly holds 135,103 KFS common shares. This total includes 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026, as disclosed in the filing footnotes.

At what price were the KFS shares purchased in this Form 4?

The 143 KFS common shares were purchased at $10.93 per share. According to the filing, the shares were acquired on April 30, 2026, through the Employee Share Purchase Plan’s open-market purchases arranged via a registered stockbroker.

What is the Kingsway Employee Share Purchase Plan mentioned in the KFS filing?

The Kingsway Employee Share Purchase Plan allows eligible employees to contribute up to 5% of adjusted salary. After 12 months’ employment, the company matches 100% of contributions and uses combined funds to buy Kingsway Financial Services shares on the open market.

Are restricted stock grants included in Kent Hansen’s KFS holdings?

Yes. The filing states that Hansen’s 135,103 direct shares include 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026. These grants form part of his total reported common stock ownership.