Results of Operations and Financial Condition. On November 5, 2026, Kingsway Corporation (the “Company”) issued a press release regarding its financial results for the three and nine month period ended September 30, 2026. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K. The information in this Current Report on Form 8-K provided under this

Results of Operations and Financial Condition. On August 6, 2026, Kingsway Corporation (the “Company”) issued a press release regarding its financial results for the three and six month period ended June 30, 2026. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K. The information in this Current Report on Form 8-K provided under this

Entry into a Material Definitive Agreement. On May 8, 2026, Kingsway Warranty Holdings LLC (“ Kingsway Seller ”), a wholly owned subsidiary of Kingsway Financial Services Inc. (“ Kingsway ”), entered into a Membership Interest Purchase Agreement (the “ Purchase Agreement ”) with Trinity Warranty Holding LLC (“ Buyer ”), pursuant to which, subject to the terms and conditions of the Purchase Agreement, Kingsway Seller sold to Buyer all of the issued and outstanding equity interests (the “ Compa…

Results of Operations and Financial Condition. On May 7, 2026, Kingsway Financial Services Inc. (the “Company”) issued a press release regarding its financial results for the three month period ended March 31, 2026. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K. The information in this Current Report on Form 8-K provided under this

Results of Operations and Financial Condition. On March 12, 2026, Kingsway Financial Services Inc. (the “Company”) issued a press release regarding its financial results for the twelve month period ended December 31, 2025. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K. The information in this Current Report on Form 8-K provided under this

and Exhibit 99.1 attached hereto shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall such information be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such filing.

and Exhibit 99.1 attached hereto shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall such information be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such filing.

Entry into a Material Definitive Agreement. Acquisition of Roundhouse Electric & Equipment Co., Inc. On July 1, 2025, Longhorns Acquisition LLC (“ Kingsway Buyer ”), a subsidiary of Kingsway Financial Services Inc. (the “ Company ”), entered into a Stock Purchase Agreement (the “ Purchase Agreement ”) with Armando Gonzales and Lee Hudson (the “ Sellers ”), pursuant to which, subject to the terms and conditions of the Purchase Agreement, Kingsway Buyer acquired from the Sellers all of the issu…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in response to

Entry into a Material Definitive Agreement. On June 24, 2025, Kingsway Financial Services Inc. (the “ Company ”) entered into a Stock Purchase Agreement (the “Purchase Agreement”) with certain entities listed on Exhibit A thereto (the “Purchasers”). Pursuant to the Purchase Agreement, the Company agreed to sell an aggregate of 1,336,264 shares of its Common Stock, par value $0.01 per share (the “Shares”) for aggregate gross proceeds of approximately $15.7 million (the “Offering”). The purchas…

Unregistered Sales of Equity Securities. The information called for by this

The offer and sale of the Class D Preferred Stock in the Private Placement was made in reliance on the exemption from registration afforded under Section 4(a)(2) of the Securities Act and/or Rule 506 of Regulation D promulgated under the Securities Act. This Current Report on Form 8-K shall not constitute an offer to sell or the solicitation of an offer to buy any securities, nor shall there be any sale of securities in any jurisdiction in which such offer, solicitation or sale would be unlaw…

Entry into a Material Definitive Agreement. Private Placement of Class D Preferred Stock On May 8, 2025, Kingsway Financial Services Inc., a Delaware corporation (the “ Company ”), entered into certain Subscription Agreements (the “ Subscription Agreements ”) pursuant to which the Company issued and sold in a private placement (the “ Private Placement ”) to accredited investors in the aggregate 80,000 shares of a newly created class of preferred stock designated Class D Preferred Stock, with…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in response to

and Exhibit 99.1 attached hereto shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall such information be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such filing.

Director — Charles Frischer: A director resigned from the board and audit committee without disagreement, which is a standard board turnover event rather than a senior executive departure.

Director — Adam Patinkin, Joshua Horowitz: The filing discloses the appointment of two new non-employee directors, which is a standard board composition change rather than an executive departure.

Results of Operations and Financial Condition. On March 17, 2025, Kingsway Financial Services Inc. (the “Company”) issued a press release regarding its financial results for the twelve month period ended December 31, 2024. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K. The information in this Current Report on Form 8-K provided under this

Entry into a Material Definitive Agreement. As disclosed on the Current Report on Form 8-K filed by Kingsway Financial Services Inc., a Delaware corporation (the “ Company ”) on February 18, 2025 (the “ Prior 8-K ”), the Company previously entered into certain Subscription Agreements (the “ Subscription Agreements ”) pursuant to which the Company issued and sold, in a private placement (the “ Private Placement ”) to accredited investors, 176,756 shares of a newly created class of preferred st…

The offer and sale of the Class C Preferred Stock in the Private Placement was made in reliance on the exemption from registration afforded under Section 4(a)(2) of the Securities Act and/or Rule 506 of Regulation D promulgated under the Securities Act. This Current Report on Form 8-K shall not constitute an offer to sell or the solicitation of an offer to buy any securities, nor shall there be any sale of securities in any jurisdiction in which such offer, solicitation or sale would be unlaw…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in response to

The offer and sale of the Class C Preferred Stock in the Private Placement was made in reliance on the exemption from registration afforded under Section 4(a)(2) of the Securities Act and/or Rule 506 of Regulation D promulgated under the Securities Act. This Current Report on Form 8-K shall not constitute an offer to sell or the solicitation of an offer to buy any securities, nor shall there be any sale of securities in any jurisdiction in which such offer, solicitation or sale would be unlaw…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in response to

Entry into a Material Definitive Agreement. Private Placement of Class C Preferred Stock On February 12, 13 and 14, 2025, Kingsway Financial Services Inc., a Delaware corporation (the “ Company ”), entered into certain Subscription Agreements (the “ Subscription Agreements ”) pursuant to which the Company issued and sold in a private placement (the “ Private Placement ”) to accredited investors in the aggregate 176,756 shares of a newly created class of preferred stock designated Class C Pref…

and Exhibit 99.1 attached hereto shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall such information be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such filing.