Common Shares, no par value

KINGSWAY FINANCIAL SERVICES INC

10 S. RIVERSIDE PLAZA, CHICAGO, IL, 60606

This is the forty-second amendment (this "Forty-Second Amendment") to the original Schedule 13D, which was filed on November 7, 2008 (the "Original Schedule 13D"), and amended on November 14, 2008 (the "First Amendment"), on November 17, 2008 (the "Second Amendment"), on November 24, 2008 (the "Third Amendment"), on December 29, 2008 (the "Fourth Amendment"), on January 12, 2009 (the "Fifth Amendment"), on February 2, 2009 (the "Sixth Amendment"), on February 17, 2009 (the "Seventh Amendment"), on February 18, 2009 (the "Eighth Amendment"), on April 9, 2009 (the "Ninth Amendment"), on April 28, 2009 (the "Tenth Amendment"), on August 4, 2009 (the "Eleventh Amendment"), on November 16, 2009 (the "Twelfth Amendment"), on April 8, 2010 (the "Thirteenth Amendment"), on April 20, 2010 (the "Fourteenth Amendment"), on June 7, 2010 (the "Fifteenth Amendment"), on June 29, 2010 (the "Sixteenth Amendment"), on September 24, 2012 (the "Seventeenth Amendment"), on November 30, 2012 (the "Eighteenth Amendment"), on June 11, 2013 (the "Nineteenth Amendment"), on September 20, 2013 (the "Twentieth Amendment"), on December 27, 2013 (the "Twenty-First Amendment"), on February 12, 2014 (the "Twenty-Second Amendment"), on September 22, 2014 (the "Twenty-Third Amendment"), on September 30, 2016 (the "Twenty-Fourth Amendment"), on December 15, 2017 (the "Twenty-Fifth Amendment"), on May 24, 2018 (the "Twenty-Sixth Amendment"), on July 19, 2018 (the "Twenty-Seventh Amendment"), on January 3, 2019 (the "Twenty-Eighth Amendment"), on March 29, 2019 (the "Twenty-Ninth Amendment"), on July 17, 2020 (the "Thirtieth Amendment"), on September 9, 2020 (the "Thirty-First Amendment"), on September 21, 2020 (the "Thirty-Second Amendment"), on June 15, 2021 (the "Thirty-Third Amendment"), on November 29, 2021 (the "Thirty-Fourth Amendment"), on March 28, 2022 (the "Thirty-Fifth Amendment"), on June 22, 2022 (the "Thirty-Sixth Amendment"), on July 18, 2022 (the "Thirty-Seventh Amendment"), on January 4, 2023 (the "Thirty-Eighth Amendment"), on March 14, 2023 (the "Thirty-Ninth Amendment"), on May 11, 2023 (the "Fortieth Amendment"), and on November 21, 2023 (the "Forty-First Amendment"). This Forty-Second Amendment is being filed jointly by Stilwell Activist Fund, L.P., a Delaware limited partnership ("Stilwell Activist Fund"); Stilwell Activist Investments, L.P., a Delaware limited partnership ("Stilwell Activist Investments"); Stilwell Associates, L.P., a Delaware limited partnership ("Stilwell Associates"); Stilwell Value Partners VII, L.P., a Delaware limited partnership ("Stilwell Value Partners VII"); Stilwell Value LLC, a Delaware limited liability company ("Stilwell Value LLC") and the general partner of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, and Stilwell Value Partners VII; and Joseph Stilwell, the managing member and owner of Stilwell Value LLC. All the filers of this statement are collectively referred to herein as the "Group." The amended joint filing agreement of the members of the Group was filed as Exhibit 31 to the Twenty-Eighth Amendment. Joseph Stilwell, a member of the Group, was appointed to the board of directors of the Issuer on April 23, 2009, and since that date he has continuously served as a director. This statement is filed by Joseph Stilwell with respect to the shares of Common Stock beneficially owned by Joseph Stilwell, including shares of Common Stock held in the names of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, and Stilwell Value Partners VII, in Joseph Stilwell's capacities as the managing member and owner of Stilwell Value LLC, which is the general partner of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, and Stilwell Value Partners VII.

The business address of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, and Stilwell Value LLC is 111 Broadway, 12th Floor, New York, New York 10006. The business address of Joseph Stilwell is 200 Calle del Santo Cristo, Segundo Piso, San Juan, Puerto Rico 00901.

The principal employment of Joseph Stilwell is investment management. Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, and Stilwell Value Partners VII are private investment partnerships engaged in the purchase and sale of securities for their own accounts. Stilwell Value LLC serves as the general partner of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, and related partnerships.

During the past five years, no member of the Group has been a party to a civil proceeding of a judicial or administrative body of competent jurisdiction and, as a result of such proceeding, was or is subject to a judgment, decree or final order enjoining future violations of, or prohibiting or mandating activities subject to, Federal or State securities laws or finding any violation with respect to such laws, except as indicated in Schedule B, attached hereto and incorporated herein by reference.

Joseph Stilwell is a citizen of the United States.

The members of the Group beneficially own an aggregate of 6,863,027 shares of Common Stock. The percentages used in this filing are calculated based on the number of outstanding shares of Common Stock, 27,572,791, reported as the number of outstanding shares as of November 6, 2024, as reported in the Issuer's Form 10-Q filed with the Securities and Exchange Commission on November 6, 2024. The purchases and sales of Common Stock reported in this item, if any, were made in open-market transactions. Each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, Stilwell Value LLC and Joseph Stilwell may be deemed to beneficially own 6,863,027 shares of Common Stock, constituting approximately 24.9% of the shares of Common Stock outstanding.

Each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, Stilwell Value LLC and Joseph Stilwell may be deemed to share the power to vote and dispose of 6,863,027 shares of Common Stock owned in the aggregate by Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, and Joseph Stilwell. Because he is the managing member and owner of Stilwell Value LLC, which is the general partner of each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII, Joseph Stilwell has the power to direct the affairs of each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII, including the voting and disposition of shares of Common Stock held in the name of each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII. Therefore, Joseph Stilwell is deemed to share voting and disposition power with each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII with regard to those shares of Common Stock. Because he is the managing member and owner of Stilwell Value LLC, Joseph Stilwell has the power to direct the affairs of Stilwell Value LLC. Stilwell Value LLC is the general partner of each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII. Therefore, Stilwell Value LLC may be deemed to share with Joseph Stilwell voting and disposition power with regard to the shares of Common Stock held by each of Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates and Stilwell Value Partners VII.

Within the past sixty days, each of Stilwell Activist Fund and Stilwell Activist Investments sold shares of Common Stock as set forth in Schedule C, attached hereto and incorporated herein by reference. Within the past sixty days, Stilwell Associates, Stilwell Value Partners VII and Joseph Stilwell did not purchase or sell any shares of Common Stock. Stilwell Value LLC has not purchased or sold any shares of Common Stock.

No person other than Stilwell Activist Fund, Stilwell Activist Investments, Stilwell Associates, Stilwell Value Partners VII, Stilwell Value LLC and Joseph Stilwell is known to have the right to receive, or the power to direct the receipt of dividends from, or proceeds from the sale of, the shares of Common Stock.

Not applicable.