Kingsway CEO buys 269 shares at $9.30 via employee plan

The employee plan permits contributions up to 5% of adjusted salary per regular payroll period and provides a 100% match after 12 months of employment.

Rhea-AI Filing Summary

Kingsway Corp President and CEO John Taylor Maloney Fitzgerald purchased 269 common shares at $9.30 per share on September 30, 2026, through Kingsway America Inc.’s Employee Share Purchase Plan; the plan administrator acquired the shares on the open market. The filing does not indicate a Rule 10b5-1 plan. His reported direct holdings after the purchase were 1,427,430 shares, including 300,000 shares of restricted stock granted March 31, 2021. Separate indirect holdings are listed as 29,100 shares each in Trust-GEF, Trust-LTF, and Trust-MPF.

Insider Trade Summary

Net Buyer: 269 shares

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 269 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock F1, F2	269	$9.30	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,427,430 shares (Direct); Common Stock — 29,100 shares (Indirect, Trust-GEF); Common Stock — 29,100 shares (Indirect, Trust-LTF); Common Stock — 29,100 shares (Indirect, Trust-MPF)

Footnotes (2)

1. F1. 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 Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.
2. F2. Includes 300,000 shares of restricted stock granted on March 31, 2021.

Key Figures

Common shares purchased: 269 shares Price per share: $9.30 per share Direct shares held after purchase: 1,427,430 shares +4 more

7 metrics

Common shares purchased 269 shares September 30, 2026

Price per share $9.30 per share Purchase on September 30, 2026

Direct shares held after purchase 1,427,430 shares Reported after the September 30, 2026 purchase

Restricted stock included in direct holdings 300,000 shares Granted March 31, 2021

Indirect trust holdings 29,100 shares each Listed for Trust-GEF, Trust-LTF, and Trust-MPF

Employee contribution limit Up to 5% of adjusted salary For each regular payroll period

Company matching contribution 100% of the employee’s contribution For employees who have worked for Kingsway America Inc. and its subsidiaries for 12 months

Key Terms

Employee Share Purchase Plan, adjusted salary, matching contribution, restricted stock

4 terms

Employee Share Purchase Plan financial

"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.

adjusted salary financial

"contribute an amount up to 5% of adjusted salary"

matching contribution financial

"make a matching contribution equal to 100%"

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.

restricted stock financial

"Includes 300,000 shares of restricted stock"

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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many KWY shares did the CEO buy, and at what price?

John Taylor Maloney Fitzgerald purchased 269 shares at $9.30 per share on September 30, 2026, through the Employee Share Purchase Plan. The plan administrator acquired the shares on the open market.

How does Kingsway’s employee share purchase plan work?

Eligible employees may contribute up to 5% of adjusted salary for each regular payroll period. For an employee who has worked for Kingsway America Inc. and its subsidiaries for 12 months, the company makes a matching contribution equal to 100% of the employee’s contribution.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/30/2026 - 04:58 PM Accepted by SEC EDGAR 09/30/2026 - 04:58 PM Learn about SEC filing dates

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 Corp [ KWY ]

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)
09/30/2026

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	09/30/2026		P		269(1)	A	$9.3	1,427,430(2)	D
Common Stock								29,100	I	Trust-GEF
Common Stock								29,100	I	Trust-LTF
Common Stock								29,100	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 Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

2. Includes 300,000 shares of restricted stock granted on March 31, 2021.

	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	09/30/2026
	** 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)