KINGSWAY Corp

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

During the quarter ended March 31, 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 February 12 through February 24, 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 240,000 shares of a newly created class of preferred stock designated Class C Preferred Stock, with a liquidation preference of $25.00 per share ("Class C Preferred Stock"), for aggregate proceeds of $6.0 million. Certain members of the Company's Board of Directors and another related party invested a total of $3.7 million in the Class C Preferred Stock private placement transaction.

KINGSWAY FINANCIAL SERVICES INC.

On March 21, 2023, the Company's Board of Directors approved a security repurchase program under which the Company was authorized to repurchase up to $10.0 million of its currently issued and outstanding securities through March 22, 2024. On March 22, 2024, the Company entered into a one year extension of its existing share repurchase program. As amended, the share repurchase program expired on March 21, 2025; however, all the authorized amount was fully utilized as of the end of January 2025. See Note 17, "Shareholders' Equity," for further discussion of the share repurchase program.

The following table provides information about our repu rchases of our securities registered pursuant to Section 12 of the Securities Exchange Act of 1934 during the quarter ended March 31, 2025.

None

Not applicable.

Item5. Other Information

During the quarter ended* March 31, 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).

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KINGSWAY FINANCIAL SERVICES INC.