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☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the fiscal year endedDecember 31, 2024 OR☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the Transition Period from _____ to _____Commission File Number001-15204Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) (I.R.S. Employer Identification No.) Chicago,IL60606(Address of principal executiveoffices)(Zip Code)1-312-766-2138(Registrant's telephone number, including area code) Securities registered pursuant to Section12(b) of the Act: Securities registered pursuant to Section12(g) of the Act: None Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule405 of the Securities Act.Yes☐No☒ Indicate by check mark if the registrant is not required to file reports pursuant to Section13 or Section15(d) of the Act.Yes☐No☒ Indicate by check mark whether the registrant (1)has filed all reports required to be filed by Section13 or 15(d) of the Securities Exchange Actof 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2)has been subjectto such filing requirements for the past 90 days.Yes☒No☐ Indicate by check mark whether the registrant has submitted electronically everyInteractive Data File required to be submitted pursuant to Rule405 of Regulation S-T (§ 232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required tosubmit such files).Yes☒No☐ Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reportingcompany, or an emerging growth company. See definitions of "large accelerated filer," "accelerated filer," "smaller reporting company," and"emerging growth company" in Rule 12b-2 of the Exchange Act. Large accelerated filer☐Accelerated filer☒Non-accelerated filer☐Smaller Reporting Company☒Emerging Growth Company☐ If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying withany new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.☐ Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of itsinternal control over financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accountingfirm that prepared or issued its audit report.☒ If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant includedin the filing reflect the correction of an error to previously issued financial statements.☐ Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensationreceived by any of the registrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b).☐ Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act).Yes☐No☒ Asof June 30,2024,the aggregate market value of the registrant's voting common stock held by non-affiliates of registrantwas$103,913,140based upon the closing sale price of the common stock as reported by the New York Stock Exchange. Solely for purposes ofthis calculation, all executive officers and directors of the registrant are considered affiliates. The number of shares, including restricted common shares, of the Registrant's Common Stock outstanding as ofMarch 17, 2025was27,537,151. DOCUMENTS INCORPORATED BY REFERENCE Part III of this Form 10-K is incorporated by reference to certain sections of the Proxy Statement for the2025Annual Meeting of Shareholders,which will be filed with the Securities and Exchange Commission no later than 120 days after the end of our fiscal year ended December 31,2024. Table Of Contents Caution Regarding Forward-Looking StatementsPART IItem 1. BusinessItem 1A. Risk FactorsItem 1B. Unresolved Staff CommentsItem 1C. CybersecurityItem 2. PropertiesItem 3. Legal ProceedingsItem 4. Mine Safety DisclosuresPART IIItem 5. Market for Registrant's Common Equity, Related Stockholder Matters and Issuer Purchases of EquitySecuritiesItem 6. ReservedItem 7. Management's Discussion and Analysis of Financial Condition and Results of OperationsItem 7A. Quantitative and Qualitative Disclosures About Market RiskItem 8. Financial Statements and Supplementary DataItem 9. Changes in and Disagreements with Accountants on Accounting and Financial DisclosureItem 9A. Controls and ProceduresItem 9B. Other InformationItem 9C. Disclosure Regarding Foreign Jurisdictions that Prevent InspectionsPART IIIItem 10. Directors, Executive Officers, and Corporate GovernanceItem 11. Executive Comp