Kingsway (NYSE: KFS) CEO adds shares through ESPP purchase

Rhea-AI Filing Summary

KINGSWAY FINANCIAL SERVICES INC President and CEO Fitzgerald John Taylor Maloney bought 211 shares of Common Stock on April 15, 2026 at $11.85 per share. The shares were acquired through the company’s Employee Share Purchase Plan, which uses employee contributions and matching company contributions to buy stock on the open market.

After this purchase, he directly holds 1,461,182 Common shares, which include 400,000 shares of restricted stock granted on March 31, 2021. He also has indirect ownership of 34,100 shares in each of three separate trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF.

Insider Trade Summary

Net Buyer: 211 shares ($2,500)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 211 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	211	$11.85	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,461,182 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF)

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 400,000 shares of restricted stock granted on March 31, 2021.

Key Figures

Shares purchased: 211 shares Purchase price: $11.85 per share Direct holdings after transaction: 1,461,182 shares +4 more

7 metrics

Shares purchased 211 shares Common Stock bought on April 15, 2026

Purchase price $11.85 per share Price for 211-share acquisition via ESPP

Direct holdings after transaction 1,461,182 shares Common Stock directly owned following April 15, 2026 trade

Restricted stock included 400,000 shares Restricted stock granted on March 31, 2021

Indirect holding Trust-GEF 34,100 shares Common Stock held indirectly in Trust-GEF

Indirect holding Trust-LTF 34,100 shares Common Stock held indirectly in Trust-LTF

Indirect holding Trust-MPF 34,100 shares Common Stock held indirectly in Trust-MPF

Key Terms

Employee Share Purchase Plan, restricted stock, open market, indirect ownership, +1 more

5 terms

Employee Share Purchase Plan financial

"The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan"

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 400,000 shares of restricted stock granted on March 31, 2021."

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.

indirect ownership financial

"direct_or_indirect": "I", "nature_of_ownership": "Trust-GEF""

Common Stock financial

"The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan"

Common stock represents ownership shares in a company, giving investors a stake in its success and a say in important decisions through voting rights. It is the most common type of stock traded on markets and can provide income through dividends, as well as potential for value growth. For investors, holding common stock means sharing in the company’s profits and risks.

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^*

Fitzgerald John Taylor Maloney

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
04/15/2026

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	04/15/2026		P		211(1)	A	$11.85	1,461,182(2)	D
Common Stock								34,100	I	Trust-GEF
Common Stock								34,100	I	Trust-LTF
Common Stock								34,100	I	Trust-MPF

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 400,000 shares of restricted stock granted on March 31, 2021.

	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	04/15/2026
	** 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 President and CEO Fitzgerald John Taylor Maloney do in this Form 4 filing?

He acquired 211 shares of KINGSWAY FINANCIAL SERVICES INC Common Stock. The shares were purchased at $11.85 each through the company’s Employee Share Purchase Plan, using employee contributions and matching company contributions to buy shares on the open market.

How many Kingsway Financial (KFS) shares does the CEO hold after this transaction?

Following the transaction, he directly holds 1,461,182 Common shares. This direct position includes 400,000 shares of restricted stock granted on March 31, 2021, in addition to other previously held shares reported in the filing as part of his overall ownership.

What is the Employee Share Purchase Plan mentioned in the KFS Form 4?

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

At what price were the KFS shares acquired by the CEO in this transaction?

The CEO’s 211 shares of Common Stock were acquired at a price of $11.85 per share. The filing explains they were purchased on the open market by the Employee Share Purchase Plan’s administrator using employee and company matching contributions.

What indirect Kingsway Financial (KFS) holdings are reported for the CEO?

The filing lists indirect ownership of 34,100 Common shares in each of three trusts: Trust-GEF, Trust-LTF, and Trust-MPF. These entries are shown as indirect holdings, separate from his direct share position in Kingsway Financial Services Inc.

What restricted stock is included in the KFS CEO’s direct holdings?

His direct holdings include 400,000 shares of restricted stock. These restricted shares were granted on March 31, 2021, and are counted within the total of 1,461,182 Common shares reported as directly owned after the reported transaction.