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    President and CEO Fitzgerald John Taylor Maloney bought $2,500 worth of shares (287 units at $8.71), increasing direct ownership by 0.02% to 1,529,074 units (SEC Form 4)

    5/1/25 4:00:08 PM ET
    $KFS
    Property-Casualty Insurers
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    Get the next $KFS alert in real time by email
    SEC FORM 4 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)
    04/30/2025
    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 04/30/2025 P 287(1) A $8.71 1,529,074(2) D
    Common Stock 20,000 I Trust-GEF
    Common Stock 20,000 I Trust-LTF
    Common Stock 20,000 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 Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald 05/01/2025
    ** 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.
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