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

Rhea-AI Filing Summary

KINGSWAY FINANCIAL SERVICES INC President and CEO John Taylor Maloney bought 244 shares of common stock at $10.22 per share in an open-market purchase made through the company’s Employee Share Purchase Plan. After this transaction, he directly owns 1,460,971 common shares.

The direct holdings figure includes 400,000 shares of restricted stock granted on March 31, 2021. In addition, Form 4 entries show 34,100 shares of common stock held indirectly in each of three trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF.

Insider Trade Summary

Net Buyer: 244 shares ($2,494)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 244 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	244	$10.22	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,460,971 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: 244 shares Purchase price: $10.22 per share Direct holdings after transaction: 1,460,971 shares +2 more

5 metrics

Shares purchased 244 shares Open-market purchase on 2026-03-30

Purchase price $10.22 per share Price for newly acquired common stock

Direct holdings after transaction 1,460,971 shares Common stock directly owned after purchase

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

Indirect holdings per trust 34,100 shares Common stock held in each of Trust-GEF, Trust-LTF, Trust-MPF

Key Terms

Employee Share Purchase Plan, restricted stock, open-market purchase, indirect ownership

4 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 purchase financial

"transaction_action": "open-market purchase""

An open-market purchase is when an investor or a company buys shares on a public stock exchange at the going market price, rather than through a private deal. It matters to investors because these purchases change how many shares are available, can push the stock price up or signal confidence from large buyers, and often affect per-share metrics like earnings—think of it like someone buying lots of apples off a grocery shelf, reducing supply and potentially raising the price.

indirect ownership financial

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

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)
03/30/2026

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	03/30/2026		P		244(1)	A	$10.22	1,460,971(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	03/31/2026
	** 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 John Taylor Maloney do in this Form 4?

John Taylor Maloney purchased 244 shares of Kingsway Financial Services common stock at $10.22 per share through an employee share purchase plan, increasing his direct holdings to 1,460,971 shares, including previously granted restricted stock and separate indirect holdings in several trusts.

How many KFS shares does the CEO directly own after this transaction?

Following the reported purchase, the CEO directly owns 1,460,971 shares of Kingsway Financial Services common stock. This total includes 400,000 shares of restricted stock that were granted on March 31, 2021, as disclosed in the Form 4 filing footnotes.

At what price did the KFS CEO buy the new shares reported on Form 4?

The CEO bought 244 additional Kingsway Financial Services common shares at a price of $10.22 per share. The filing explains these shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, with purchases executed in the open market by the plan administrator.

What is the Kingsway employee share purchase plan mentioned in the KFS Form 4?

The Kingsway America Inc. Employee Share Purchase Plan allows eligible employees to contribute up to 5% of adjusted salary, with the company matching 100% after 12 months of employment. Combined contributions are then used to buy Kingsway Financial Services shares on the open market.

Does the KFS CEO have any restricted stock included in his holdings?

Yes. The filing notes that his direct holdings of 1,460,971 common shares include 400,000 shares of restricted stock granted on March 31, 2021. This restricted stock is part of his overall equity position in Kingsway Financial Services as reported in the Form 4 footnotes.

What indirect KFS share holdings are reported for the CEO in this Form 4?

The Form 4 lists indirect ownership of 34,100 Kingsway Financial Services shares in each of three separate trusts called Trust-GEF, Trust-LTF, and Trust-MPF. These entries are categorized as indirect holdings and are distinct from the CEO’s directly owned shares.