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 September 11, 2023 – Kingsway Announces Formation of Vertical Market Solutions, LLC (“VMS”) and Acquisition of Systems Products International, Inc. / Kingsway Search Xclerator Announces Addition of Miles Mamon
 August 8, 2023 – Kingsway Reports Second Quarter 2023 Financial Results
 August 1, 2022 – Kingsway to Report Financial Results for Second Quarter 2023 on August 8, 2023
 June 12, 2023 – Kingsway Set to Join Russell 3000® and Russell 2000® Indexes
 May 22, 2023 – Kingsway to Present at the Ld Micro Investor Conference in Los Angeles on June 7, 2023, at 4:00pm Pacific Time
 May 15, 2023 – Kingsway Publishes Investor Day Presentation to Company Website
 May 9, 2023 – Kingsway Reports First Quarter 2023 Financial Results
 May 3, 2023 – Kingsway Publishes Updated Investor Presentation To Company Website
 May 2, 2023 – Kingsway to Report Financial Results for First Quarter 2023 on May 9, 2023
 May 2, 2023 – Kingsway Search Xclerator Announces Addition of Peter Hearne and Charles Joyce
 April 19, 2023 – Kingsway Announces Investor Day and Fireside Chat With Will Thorndike at the New York Stock Exchange on May 16, 2023
 April 17, 2023 – Kingsway Announces Availability of Annual Letter to Shareholders
 March 21, 2023 – Kingsway Financial Services Inc. Board of Directors Authorizes Share Repurchase Plan
 March 20, 2023 – Kingsway has Repurchased $74.6 Million of its Trust Preferred Debt and $21 Million of Deferred Interest – Remaining $0.9 Million of Principal Expected to be Repurchased in Coming Days
 March 8, 2023 – Kingsway Reports Full Year 2022 Financial Results
 March 6, 2023 – Kingsway to Report Financial Results for Full Year 2022 on March 8, 2023
 January 18, 2023 – Kingsway Publishes Updated Investor Presentation To Company Website
 January 9, 2023 – Kingsway Welcomes Sun Mountain Partners, LLC, Led by Will Thorndike and Christian Solberg, as a Large Investor in Kingsway