KINGSWAY Corp (KFS) CEO adds shares through employee stock purchase plan

Rhea-AI Filing Summary

KINGSWAY Corp President and CEO John Taylor Maloney increased his stake through the company’s employee share plan. On May 29, he bought 250 shares of Common Stock in an open-market purchase at $10.03 per share under the Employee Share Purchase Plan.

After this transaction, his direct ownership rose to 1,455,634 Common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. He also reports indirect holdings of 29,100 shares of Common Stock in each of three family trusts labeled MPF, LTF, and GEF.

Insider Trade Summary

Net Buyer: 250 shares ($2,508)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 250 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	250	$10.03	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,455,634 shares (Direct, null); Common Stock — 29,100 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 Corporation 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: 250 shares Purchase price: $10.03 per share Direct holdings after trade: 1,455,634 shares +4 more

7 metrics

Shares purchased 250 shares Common Stock bought on May 29, 2026

Purchase price $10.03 per share Open-market purchase under ESPP

Direct holdings after trade 1,455,634 shares Common Stock directly owned after purchase

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

Indirect trust holdings 29,100 shares Common Stock per trust (MPF, LTF, GEF)

Employee contribution limit 5% of adjusted salary Maximum ESPP contribution per payroll period

Company match rate 100% of employee contributions For employees with 12 months of service

Key Terms

Employee Share Purchase Plan, restricted stock, open market, Trust-MPF, +2 more

6 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 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.

Trust-MPF financial

"Common Stock ... total_shares_following_transaction 29100.0000 ... nature_of_ownership Trust-MPF"

Trust-LTF financial

"Common Stock ... total_shares_following_transaction 29100.0000 ... nature_of_ownership Trust-LTF"

Trust-GEF financial

"Common Stock ... total_shares_following_transaction 29100.0000 ... nature_of_ownership Trust-GEF"

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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 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)
05/29/2026

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	05/29/2026		P		250(1)	A	$10.03	1,455,634(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 400,000 shares of restricted stock granted on March 31, 2021.

	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	06/01/2026
	** 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 insider transaction did KINGSWAY Corp (KFS) report for John Taylor Maloney?

KINGSWAY Corp reported that President and CEO John Taylor Maloney bought 250 Common shares. The shares were purchased on May 29 through an open-market transaction executed under the company’s Employee Share Purchase Plan, increasing his directly held position in the stock.

At what price did the KINGSWAY Corp (KFS) CEO acquire new shares?

The CEO acquired 250 KINGSWAY Corp Common shares at $10.03 per share. This price reflects the cost of shares purchased on the open market under the Employee Share Purchase Plan, which uses combined employee and matching company contributions to buy stock.

How many KINGSWAY Corp (KFS) shares does the CEO own after this Form 4 filing?

After the reported transaction, John Taylor Maloney directly owns 1,455,634 Common shares of KINGSWAY Corp. This total includes 400,000 restricted shares granted on March 31, 2021, in addition to unrestricted Common Stock previously accumulated.

What is the KINGSWAY Corp (KFS) Employee Share Purchase Plan mentioned in the filing?

The Employee Share Purchase Plan allows eligible employees to contribute up to 5% of adjusted salary, with a 100% company match after 12 months of service. Combined contributions are then used to buy KINGSWAY Corp shares on the open market via a registered broker.

What indirect KINGSWAY Corp (KFS) holdings does the CEO report in the trusts?

The Form 4 shows indirect ownership of 29,100 Common shares in each of three trusts identified as Trust-MPF, Trust-LTF, and Trust-GEF. These entries reflect trust-held positions, separate from the CEO’s directly owned KINGSWAY Corp shares reported in his name.

How many restricted KINGSWAY Corp (KFS) shares are included in the CEO’s direct holdings?

Within the CEO’s reported 1,455,634 directly held Common shares, 400,000 shares are restricted stock granted on March 31, 2021. Restricted stock typically vests over time or upon meeting specific conditions defined in the company’s equity compensation arrangements.