KINGSWAY FINANCIAL SERVICES INC

There have been no material changes with respect to those risk factors previously disclosed in our 2024 Annual Report.

During the quarter ended June 30, 2025, the Company issued equity securities that were not registered under the Securities Act of 1933, as amended (the "Securities Act"), as described below. These transactions did not involve any underwriters, underwriting discounts or commissions, or any public offering. The transactions described below were exempt from the registration requirements of the Securities Act either under Section 4(a)(2) of the Securities Act and/or Rule 506 of Regulation D promulgated thereunder. All recipients had adequate access, through their relationships with the Company, to information about the Company.

On May 8, 2025, the Company entered into certain Subscription Agreements pursuant to which the Company issued and sold in a 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 a liquidation preference of $25.00 per share ("Class D Preferred Stock"), for aggregate proceeds of $2.0 million. Certain members of the Company's Board of Directors invested a total of $2.0 million in the Class D Preferred Stock private placement transaction

On June 24, 2025, the Company entered into a Stock Purchase Agreement pursuant to which the Company issued and sold in a private placement to accredited investors in the aggregate 1,336,264 shares of its Common Stock, for aggregate proceeds of $15.7 million. The purchase price for each share of Common Stock was $11.75 per share. Net proceeds to the Company were $15.6 million after deducting offering expenses.

None

Not applicable.

Item5. Other Information

During the quarter ended* June 30, 2025*, no director or officer (as defined in Rule16a-1(f) under the Exchange Act) of the Company adopted, modified or terminated a “Rule10b5-1 trading arrangement” or “non-Rule10b5-1 trading arrangement” (as each term is defined in Item408 of Regulation S-K).