Presentation to be Held In-Person at the New York Stock Exchange as well as Virtually

Chicago, (April 19, 2023) – (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that the Company will host an Investor Day on Tuesday, May 16, 2023.

President and Chief Executive Officer, John T. Fitzgerald, along with Kent A. Hansen, Executive Vice President and Chief Financial Officer and members of the management team will discuss a range of topics covering the Company’s operations, long-term growth strategy and financial structure. Prepared presentations will begin at 9:30 am ET.

CEO John T. Fitzgerald will also host a fireside chat with Will Thorndike, Managing Partner of The Cromwell Harbor Partnership, author of “The Outsiders, Eight Unconventional CEOs and Their Radically Rational Blueprint for Success”, and member of the Kingsway Search Xcelerator (“KSX”) advisory board, to discuss a range of topics including capital allocation, the power of long holding periods, and his experience as an original and long-time investor in the Search Fund ecosystem.

Event Location / Details
The event will take place at the New York Stock Exchange (RSVP required) and will also be available virtually at the investors section on the company website: https://kingsway-financial.com/

Interested Parties
Individuals interested in attending or registering for the event may contact James Carbonara, Hayden IR at james@haydenir.com or by calling (646) 755-7412.

A live webcast, including video, audio and presentation slides, will be accessible on https://kingsway-financial.com at the time of the meeting. Those who attend virtually will also have the opportunity to participate in the question-and-answer session following the presentation.

Contact
Hayden IR
James Carbonara
(646) 755-7412
james@haydenir.com

OR

Kingsway Financial Services Inc.
Kent Hansen, CFO
(312) 766-2163
khansen@kingsway-financial.com