Common Stock, $0.01 par value per share

KINGSWAY FINANCIAL SERVICES INC

10 S. RIVERSIDE PLAZA, SUITE 1520, CHICAGO, IL, 60606

(a) Item 5(a) and 5(b) of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following: As of the close of business on December 17, 2025, the Reporting Persons may be deemed to beneficially own, in the aggregate, 2,386,119 Shares, representing approximately 8.24% of the Issuer's outstanding Shares (based upon the 28,956,152 Shares stated to be outstanding as of November 6, 2025 in the Issuer's Form 10-Q dated November 6, 2025 for the quarter ended September 30, 2025 plus 315,789 Shares issuable upon exercise of the Reporting Persons' Series B Warrants and conversion of the Report Persons' Class C Preferred Shares). Oakmont has sole voting power and sole dispositive power with respect to the 2,303,619 Shares that it owns directly. Oakmont may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group. EJK has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. EJK may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group. 1272562 has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of its ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. 1272562 may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group. Mr. Kavanagh has sole voting power and sole dispositive power with respect to 34,750 Shares owned through a self-directed Retirement Savings Plan. Mr. Kavanagh has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of Mr. Kavanagh's ownership of all the outstanding voting stock of EJK, and EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. Mr. Kavanagh may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group. Mr. Kavanagh's sister owns directly and through a registered retirement savings account 13,500 Shares as to which Mr. Kavanagh disclaims beneficial ownership. Mr. Hannon has sole voting power and sole dispositive power with respect to the following 34,000 Shares: (i) the 29,500 Shares owned directly by him or through a self-directed Retirement Savings Plan; and (ii) the 4,500 Shares owned directly by two trusts for Mr. Hannon's children; Mr. Hannon is the sole trustee of each such trust. Mr. Hannon has shared voting power and shared dispositive power with respect to the following 2,317,369 Shares: (i) the 2,303,619 Shares owned directly by Oakmont, by virtue of his ownership of all of the capital stock of 1272562, and 1272562's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont; and (ii) the 13,750 Shares owned directly by Mr. Hannon's spouse. Mr. Hannon may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group.

The information set forth in Item 5(a) of this Amendment No. 6 is incorporated herein by reference.

The information set forth in Item 4 of this Amendment No. 6 is incorporated herein by reference.