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SCHEDULE 13D/A 0001538186 XXXXXXXX LIVE 6 Common Stock, $0.01 par value per share 12/17/2025 false 0001072627 496904202 KINGSWAY FINANCIAL SERVICES INC 10 S. RIVERSIDE PLAZA, SUITE 1520 CHICAGO IL 60606 Terence M. Kavanagh (416) 923-1477 45 St. Clair Avenue West, Suite 400 Toronto A6 M4V 1K9 Y Oakmont Capital Inc. a WC N A6 2303619.00 0.00 2303619.00 0.00 2386119.00 N 8.24 CO In reference to Rows 11 and 13 above, see Item 5 herein. Y E.J.K. Holdings Inc. a WC N A6 0.00 2303619.00 0.00 2303619.00 2386119.00 N 8.24 CO In reference to Rows 11 and 13 above, see Item 5 herein. Y 1272562 Ontario Inc a WC N A6 0.00 2303619.00 0.00 2303619.00 2386119.00 N 8.24 CO In reference to Rows 11 and 13 above, see Item 5 herein. Y Terence M. Kavanagh a PF N Z4 34750.00 2303619.00 34750.00 2303619.00 2386119.00 Y 8.24 IN In reference to Rows 11, 12 and 13 above, see Item 5 herein. 0001538186 N Gregory P. Hannon a PF N Z4 34000.00 2317369.00 34000.00 2317369.00 2386119.00 N 8.24 IN In reference to Rows 11 and 13 above, see Item 5 herein. Common Stock, $0.01 par value per share KINGSWAY FINANCIAL SERVICES INC 10 S. RIVERSIDE PLAZA, SUITE 1520 CHICAGO IL 60606 This Amendment No. 6 to Schedule 13D (this "Amendment") amends the Statement on Schedule 13D filed on March 5, 2009, as previously amended on December 12, 2012, September 13, 2013, September 20, 2013, March 21, 2019 and April 9, 2025 (the "Schedule 13D") by Oakmont Capital Inc., an Ontario corporation ("Oakmont"), E.J.K. Holdings Inc., an Ontario corporation ("EJK"), 1272562 Ontario Inc., an Ontario corporation ("1272562"), and Gregory P. Hannon and Terence M. Kavanagh, each of whom is a citizen of Canada (collectively, the "Reporting Persons"). Capitalized terms used herein not otherwise defined shall have the meaning ascribed to them in the Schedule 13D. All references to common stock in this Amendment have been adjusted for the rights offering which expired on September 6, 2013 (the "Rights Offering"). Item 4 of this Schedule 13D is hereby supplemented as follows: On December 17, 2025, the option agreement described in Item 6 of this Amendment No. 6 was exercised. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special (as hereafter defined) at a price of US$8.25 per Share. Except as disclosed in Item 6 of this Amendment No. 6, the Reporting Persons have no current plans or proposals which relate to or would result in any of the events described in Items (a) through (j) of the instructions to Item 4 of Schedule 13D. The information set forth in Item 6 of this Amendment No. 6 is incorporated herein by reference. (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. Item 6 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following: On December 17, 2025, David Capital Partners Special Situation Fund, LP ("DCP Special") exercised in full the option agreement with Oakmont filed as Exhibit 99.1 to Amendment No. 5 to the 13D. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special at a price of US$8.25 per Share. Oakmont Capital Inc. /s/ Terence M. Kavanagh Terence M. Kavanagh, President 12/17/2025 E.J.K. Holdings Inc. /s/ Terence M. Kavanagh Terence M. Kavanagh, President 12/17/2025 1272562 Ontario Inc /s/ Gregory P. Hannon Gregory P. Hannon, President 12/17/2025 Terence M. Kavanagh /s/ Terence M. Kavanagh Terence M. Kavanagh 12/17/2025 Gregory P. Hannon /s/ Gregory P. Hannon Gregory P. Hannon 12/17/2025