KINGSWAY FINANCIAL (NYSE: KFS) CEO adds shares through ESPP open-market buy

Rhea-AI Filing Summary

Kingsway Financial Services Inc. President and CEO John Taylor Maloney bought 234 shares of common stock on March 13, 2026 in an open-market purchase at $10.71 per share. This increased his directly held stake to 1,460,727 common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021.

The filing also shows indirect ownership of 34,100 common shares in each of three separate trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF. The newly acquired shares were purchased through the Kingsway America Inc. Employee Share Purchase Plan, where employee payroll contributions are matched by the company and used to buy shares on the open market.

Insider Trade Summary

Net Buyer: 234 shares ($2,506)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 234 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	234	$10.71	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,460,727 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.

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 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)

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

3. Date of Earliest Transaction (Month/Day/Year)
03/13/2026

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	03/13/2026		P		234(1)	A	$10.71	1,460,727(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	03/16/2026
	** 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.

FAQ

What insider transaction did KFS President and CEO John Maloney report?

John Taylor Maloney reported buying 234 shares of KINGSWAY FINANCIAL SERVICES INC common stock. The purchase occurred on March 13, 2026 at $10.71 per share in an open-market transaction, modestly increasing his direct equity stake in the company.

How many KFS shares does CEO John Maloney hold after this Form 4?

After the reported transaction, John Taylor Maloney directly holds 1,460,727 shares of KINGSWAY FINANCIAL SERVICES INC common stock. This total includes 400,000 restricted shares that were originally granted on March 31, 2021 as part of his long-term equity compensation.

How were the newly acquired KFS shares purchased by the CEO?

The 234 newly acquired shares were purchased through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Under this plan, eligible employees contribute up to 5% of adjusted salary, which the company matches 100%, and a broker buys shares on the open market.

Does the KFS CEO have indirect share ownership through trusts?

Yes. The filing lists indirect ownership of 34,100 KFS common shares in each of three trusts: Trust-GEF, Trust-LTF, and Trust-MPF. These entries reflect additional holdings associated with the CEO beyond his directly held stock position.

What does the transaction code on the KFS Form 4 indicate?

The transaction uses code P, described as a purchase in open market or private transaction. Combined with Form 4 data, this confirms the CEO made an open-market buy of 234 KFS common shares at a price of $10.71 per share.

What is the matching contribution feature of the KFS ESPP mentioned in the Form 4?

Under the ESPP, eligible employees may contribute up to 5% of adjusted salary each pay period. After 12 months of employment, the company matches 100% of employee contributions, and both contributions are used to purchase KFS shares on the open market through a registered broker.