UNITED STATES
SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

The Securities Exchange Act of 1934 (Amendment No.    )

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

KINGSWAY FINANCIAL SERVICES INC.

(Name of Registrant as Specified in Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS OF

KINGSWAY FINANCIAL SERVICES INC.

PROXY STATEMENT

FOR THE MEETING TO BE HELD ON TUESDAY, MAY 16, 2023

DATED APRIL 6, 2023

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

NOTICE IS HEREBY GIVEN THAT an annual meeting (the “Meeting”) of the shareholders of Kingsway Financial Services Inc. (the “Corporation”) will be held at 9:00 a.m. Eastern Time (8:00 a.m. Central time) on Tuesday, May 16, 2023. The Meeting will be held through virtual means and in person at the New York Stock Exchange. If you choose to attend and participate in the Meeting virtually, you can vote your shares electronically and submit your questions prior to and during the Meeting by visiting: meetnow.global/MZVHWJG at the Meeting date and time described in the accompanying proxy statement. The purpose of the Meeting is to:

We may also transact such other business as may properly come before the Meeting and any postponements or adjournments thereof.

The accompanying proxy statement provides additional information relating to the matters to be dealt with at the Meeting and is deemed to form part of this Notice of Annual Meeting of Shareholders (the “Notice of Meeting”).

Only shareholders of record at the close of business on March 22, 2023 are entitled to notice of the Meeting and to vote at the Meeting or any adjournment or postponement thereof.

SHAREHOLDERS WHO ARE UNABLE TO ATTEND THE MEETING SHOULD COMPLETE, DATE AND SIGN THE ENCLOSED FORM OF PROXY AND RETURN IT IN THE ENVELOPE PROVIDED FOR THAT PURPOSE, OR VOTE BY TELEPHONE OR OVER THE INTERNET.

Proxies to be used at the Meeting must be deposited with Computershare Investor Services Inc., PO BOX 43006 , Canton, MA, 02021 , before 9:00 a.m. ET (8:00 a.m. CT) on May 16, 2023, or if the Meeting is adjourned or postponed, no later than 4:00 p.m. (Central time) on the second business day preceding the day to which the Meeting is adjourned or postponed. The proxy voting cut-off may be waived or extended by the Chairman of the Board at his discretion without notice.

IMPORTANT NOTICE REGARDING THE INTERNET AVAILABILITY OF PROXY MATERIALS FOR THE MEETING OF SHAREHOLDERS TO BE HELD ON MAY 16, 2023.

The proxy statement and our 2022 Annual Report on Form 10-K, including all amendments thereto, are available on our website, www.kingsway-financial.com.

TABLE OF CONTENTS

LETTER TO SHAREHOLDERS

April 6, 2023

Dear Shareholder,

I would like to invite you to join the board of directors and senior management of Kingsway Financial Services Inc. at our next annual meeting of shareholders (the “Meeting”), which convenes at 9:00 a.m. ET (8:00 a.m. CT) on Tuesday, May 16, 2023.

The Meeting will be held in person at the New York Stock Exchange, Hamilton Room, 11 Wall St, New York, NY 10005. Shareholders who attend in person will be required to show a government issued photo ID and should enter through the security tent at 18 Broad Street, New York, NY 10005. The Meeting will also be held virtually and you will be able to attend and participate in the Meeting virtually, vote your shares electronically and submit your questions prior to and during the Meeting by visiting: meetnow.global/MZVHWJG at the Meeting date and time described in the accompanying proxy statement.

At the Meeting, you will be asked to elect seven (7) directors, ratify the appointment of Plante & Moran, PLLC as our independent registered public accounting firm for the 2023 fiscal year, and consider the approval of the 2022 compensation of the named executive officers on a non-binding and advisory basis.

Whether or not you plan to attend the Meeting, please complete, date, sign, and return, as promptly as possible, the enclosed form of proxy in the accompanying reply envelope or vote by telephone or the Internet. If you attend the Meeting, vote electronically at that time and/or complete a new form of proxy bearing a later date and properly submit it before the deadline, your vote will revoke any proxy previously submitted.

I appreciate your participation.

Sincerely,

Terence M. Kavanagh

Chairman of the Board of Directors

GENERAL PROXY INFORMATION

SOLICITATION OF PROXIES

This proxy statement (the “Proxy Statement”) is furnished in connection with the solicitation of proxies by or on behalf of the management and the board of directors (the “Board”) of Kingsway Financial Services Inc. (the “Corporation,” “Kingsway,” “us,” or “we”) for use at the annual meeting (the “Meeting”) of shareholders of the Corporation (the “shareholders”) to be held on Tuesday, May 16, 2023 at 9:00 a.m. ET (8:00 a.m. CT), or any adjournment or postponement thereof, for the purposes set out in the accompanying notice of meeting (the “Notice of Meeting”). The meeting will be held at the New York Stock Exchange, Hamilton Room, 11 Wall St, New York, NY 10005, and virtually. You will be able to attend and participate in the Meeting, vote your shares electronically and submit your questions prior to and during the Meeting by visiting: meetnow.global/MZVHWJG at the Meeting date and time described in the accompanying Proxy Statement. The form of proxy and the Proxy Statement are being sent to shareholders on or about April 6, 2023.

The solicitations will be made primarily by mail, but proxies may also be solicited personally or by telephone by directors, officers, and regular employees of the Corporation, none of whom will receive additional compensation for assisting with the solicitation, and the estimated cost of which will be nominal. Banks, brokers, custodians, nominees and fiduciaries will be requested to forward the proxy soliciting materials to beneficial owners, and the Corporation will reimburse such persons for such reasonable out-of-pocket expenses incurred by them. The expenses of soliciting proxies, including the cost of preparing, assembling and mailing the Proxy Statement to shareholders, will be borne by the Corporation.

QUORUM

A quorum is required in order for the Meeting to be properly constituted. Holders of record, either personally present or represented by proxy, of not less than a majority of the voting power of the issued and outstanding shares of capital stock of the Corporation entitled to vote thereat shall constitute a quorum for the transaction of business at the Meeting.

VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF

The authorized capital of the Corporation consists of 50,000,000 shares of common stock, par value $0.01 per share (the “Shares” or “Common Shares”), and 1,000,000 shares of preferred stock, par value $0.01 per share, issuable in series, of which 222,876 shares have been designated as Class A Preferred Stock, Series 1 (the “Preferred Shares”). As of the close of business on March 22, 2023, the record date for the Meeting (the “Record Date”), 25,854,466 Common Shares were outstanding, of which 500,000 Common Shares, representing approximately 1.9% of the Common Shares, are currently restricted from voting pursuant to that certain Restricted Stock Agreement, dated as of September 5, 2018, by and between the Corporation and John T. Fitzgerald (the “2018 Fitzgerald Restricted Stock Agreement”), as described below. Therefore, as of the Record Date there were 25,354,466 Common Shares outstanding and entitled to one (1) vote each at the Meeting. The Common Shares are listed on the New York Stock Exchange (the “NYSE”) under the symbol “KFS.”

As of the Record Date, there were 30,000 Preferred Shares issued and outstanding. Each Preferred Share is convertible into 6.25 Common Shares, subject to adjustment in accordance with the Corporation’s Certificate of Incorporation. The holders of the 30,000 Preferred Shares issued and outstanding have submitted a Notice of Intent to convert their Preferred Shares to Common Shares; however, the conversion process was not completed prior to the Record Date. The outstanding Preferred Shares are not entitled to vote at the Meeting.

Mr. John T. Fitzgerald holds 500,000 Common Shares subject to certain vesting restrictions, which were granted to him pursuant to the 2018 Fitzgerald Restricted Stock Agreement (each a “2018 Fitzgerald Restricted Common

Share”). The 2018 Fitzgerald Restricted Common Shares shall become fully vested, and the Fitzgerald Restriction Period (as defined below) shall lapse, as of March 28, 2024 if Mr. Fitzgerald remains in continuous employment with the Corporation through such date (the “2018 Fitzgerald Vesting Date”). During the period between the date of grant and the Fitzgerald Vesting Date (the “2018 Fitzgerald Restriction Period”), Mr. Fitzgerald may not sell, transfer, assign, pledge, hypothecate, or otherwise encumber or dispose of the 2018 Fitzgerald Restricted Common Shares, except as provided in the 2018 Fitzgerald Restricted Stock Agreement or the Corporation’s 2013 Equity Incentive Plan dated December 4, 2013 (as amended) (the “2013 Equity Incentive Plan”). Mr. Fitzgerald has all rights as a shareholder of the Corporation during the 2018 Fitzgerald Restriction Period in respect of the 2018 Fitzgerald Restricted Common Shares, including, but not limited to, the right to receive dividends and other distributions and the right to participate in any capital adjustment applicable to all holders of Common Shares; provided, however, that he may not vote the 2018 Fitzgerald Restricted Common Shares until the 2018 Fitzgerald Vesting Date and any dividends paid or other distribution with respect to the 2018 Fitzgerald Restricted Common Shares shall be deposited with the Corporation and shall be subject to the same restrictions as the 2018 Fitzgerald Restricted Common Shares with respect to which such distribution was made. Pursuant to the terms of the 2013 Equity Incentive Plan, if a Change in Control (as defined in the 2013 Equity Incentive Plan) occurs, all outstanding 2018 Fitzgerald Restricted Common Shares shall immediately become fully vested and the 2018 Fitzgerald Restriction Period applicable to such 2018 Fitzgerald Restricted Common Shares shall lapse.

Mr. John T. Fitzgerald also holds 600,000 Common Shares subject to certain vesting restrictions (the “2021 Fitzgerald Restricted Common Shares”) that were granted to him pursuant to that certain Restricted Stock Agreement, dated as of March 31, 2021, by and between the Corporation and Mr. Fitzgerald (the “2021 Fitzgerald Restricted Stock Agreement”). The original grant of 1,000,000 2021 Fitzgerald Restricted Common Shares vests as follows: 200,000 2021 Fitzgerald Restricted Common Shares vested on the date of the grant and the remaining 800,000 2021 Fitzgerald Restricted Common Shares shall vest equally in 100,000 share tranches every September 5, until 2028, such that on September 5, 2028 all 2021 Fitzgerald Restricted Common Shares shall become fully vested and the 2021 Fitzgerald Restriction Period (as defined below) shall lapse. During the period between the date of grant and the date upon which any 2021 Fitzgerald Restricted Common Shares vest (the “2021 Fitzgerald Restriction Period”), Mr. Fitzgerald may not assign or transfer any unvested 2021 Fitzgerald Restricted Common Shares, except as provided in the 2021 Fitzgerald Restricted Stock Agreement or the Corporation’s 2020 Equity Incentive Plan dated September 21, 2020 (the “2020 Equity Incentive Plan”). Mr. Fitzgerald has all rights as a shareholder of the Corporation during the 2021 Fitzgerald Restriction Period in respect of the 2021 Fitzgerald Restricted Common Shares, including, but not limited to, the right to receive dividends and other distributions and the right to participate in any capital adjustment applicable to all holders of Common Shares; provided, however, that any dividends paid or other distribution with respect to the 2021 Fitzgerald Restricted Common Shares shall be deposited with the Corporation and shall be subject to the same restrictions as the 2021 Fitzgerald Restricted Common Shares with respect to which such dividend or other distribution was made. Mr. Fitzgerald is entitled to vote the 2021 Fitzgerald Restricted Common Shares at the Meeting.

Mr. Kent A. Hansen holds 21,836 Common Shares subject to certain vesting restrictions (the “2021 Hansen Restricted Common Shares”) that were granted to him pursuant to that certain Restricted Stock Agreement, dated as of December 3, 2021, by and between the Corporation and Mr. Hansen (the “2021 Hansen Restricted Stock Agreement”). The original grant of 32,754 2021 Hansen Restricted Common Shares shall equally vest in 10,918 tranches every December 3, until 2024, such that on December 3, 2024 all the 2021 Hansen Restricted Common Shares shall become fully vested, and the 2021 Hansen Restriction Period (as defined below) shall lapse with respect to such remaining 2021 Hansen Restricted Common Shares, on December 3, 2024. During the period between the date of grant and the date upon which any 2021 Hansen Restricted Common Shares vest (the “2021 Hansen Restriction Period”), Mr. Hansen may not assign or transfer the 2021 Hansen Restricted Common Shares, except as provided in the 2021 Hansen Restricted Stock Agreement or the 2020 Equity Incentive Plan. Mr. Hansen has all rights as a shareholder of the Corporation during the 2021 Hansen Restriction Period in respect of the 2021 Hansen Restricted Common Shares, including, but not limited to, the right to receive dividends and other distributions and the right to participate in any capital adjustment applicable to all holders of Common Shares; provided, however, that any

dividends paid or other distribution with respect to the 2021 Hansen Restricted Common Shares shall be deposited with the Corporation and shall be subject to the same restrictions as the 2021 Hansen Restricted Common Shares with respect to which such dividend or other distribution was made. Mr. Hansen is entitled to vote the 2021 Hansen Restricted Common Shares at the Meeting.

Mr. Kent A. Hansen also holds 25,111 Common Shares subject to certain vesting restrictions (the “2022 Hansen Restricted Common Shares”) that were granted to him pursuant to that certain Restricted Stock Agreement, dated as of December 15, 2022, by and between the Corporation and Mr. Hansen (the “2022 Hansen Restricted Stock Agreement”). 25,111 2022 Hansen Restricted Common Shares shall vest ratably in tranches of 8,370 2022 Hansen Restricted Common Shares each, every December 1, (the first tranche will vest 8,371 2022 Hansen Restricted Common Shares) until 2025, such that on December 1, 2025 all the 2022 Hansen Restricted Common Shares shall become fully vested, and the 2022 Hansen Restriction Period (as defined below) shall lapse with respect to such remaining 2022 Hansen Restricted Common Shares, on December 1, 2025. During the period between the date of grant and the date upon which any 2022 Hansen Restricted Common Shares vest (the “2022 Hansen Restriction Period”), Mr. Hansen may not assign or transfer the 2022 Hansen Restricted Common Shares, except as provided in the 2022 Hansen Restricted Stock Agreement or the 2020 Equity Incentive Plan. Mr. Hansen has all rights as a shareholder of the Corporation during the 2022 Hansen Restriction Period in respect of the 2022 Hansen Restricted Common Shares, including, but not limited to, the right to receive dividends and other distributions and the right to participate in any capital adjustment applicable to all holders of Common Shares; provided, however, that any dividends paid or other distribution with respect to the 2022 Hansen Restricted Common Shares shall be deposited with the Corporation and shall be subject to the same restrictions as the 2022 Hansen Restricted Common Shares with respect to which such dividend or other distribution was made. Mr. Hansen is entitled to vote the 2022 Hansen Restricted Common Shares at the Meeting.

Security Ownership of Certain Beneficial Owners and Management

In accordance with U.S. securities laws, the following table sets forth certain information regarding beneficial ownership or control or direction, directly or indirectly, of the Common Shares as of the Record Date, by each shareholder (other than those shareholders for whom information is provided in the subsequent table) known by the Corporation to be a beneficial owner of more than 5% of the Corporation’s outstanding Common Shares.

In accordance with U.S. securities laws, the following table sets forth certain information regarding beneficial ownership or control or direction, directly or indirectly, of the Common Shares as of the Record Date, by: (i) each director and director nominee of the Corporation; (ii) the Chief Executive Officer and each additional executive officer named under the heading “2022 Summary Compensation Table” in the Proxy Statement; and (iii) all directors, director nominees and executive officers of the Corporation as a group. The Corporation believes that, except as otherwise noted, each individual named has sole investment and voting power with respect to the Common Shares indicated as beneficially owned by such individual. Unless otherwise indicated, the business address of each named person is: 10 S. Riverside Plaza, Suite 1520, Chicago Illinois 60606.

* Indicates less than 1%.

Notes:

Q&A ON PROXY VOTING

You are entitled to attend the Meeting only if you were a shareholder of the Corporation as of the close of business on the Record Date, or if you hold a valid proxy for the Meeting.

The in-person Meeting will begin promptly at 9:00 a.m. ET (8:00 a.m. CT).

You will be able to attend the Meeting virtually and submit your questions during the Meeting by visiting meetnow.global/MZVHWJG.

To participate in the Meeting, you will need to review the information included on your Notice of Meeting, on your proxy card or on the instructions that accompanied your proxy materials.

If you hold your Shares through an intermediary, such as a bank or broker, you must register in advance using the instructions below.

The online Meeting will begin promptly at 9:00 a.m. ET (8:00 a.m. CT). If you are attending virtually, we encourage you to access the Meeting prior to the start time leaving ample time for the check in. Please follow the registration instructions as outlined in this Proxy Statement.

If you hold your Shares through an intermediary, such as a bank or broker, you must register in advance to attend the Meeting in person and online.

To register to attend the Meeting virtually by webcast you must submit proof of your proxy power (legal proxy) reflecting your Shareholdings along with your name and email address to Computershare. Requests for registration must be labeled as “Legal Proxy” and be received no later than 4:00 p.m. (Central time) on May 11, 2023.

You will receive a confirmation of your registration by email after we receive your registration materials.

Requests for registration should be directed to us at the following:

By email: legalproxy@computershare.com

Forward the email from your broker, or attach an image of your legal proxy, to

By mail:

Computershare

Kingsway Financial Services Inc. Legal Proxy

P.O. Box 43001

Providence, RI 02940-3001

Computershare Investor Services

150 Royall Street, Suite 101

Canton, MA, 02021

If you are a beneficial shareholder, the intermediary (usually a bank, trust company, broker, securities dealer or other financial institution) through which you hold your Shares will send you instructions on how to vote your Shares. Please follow the instructions on your voting instruction form.

If you have signed the form of proxy but have not specified on the form of proxy how you want your Shares to be voted on a particular issue, then your proxyholder will vote your Shares in favor of: (i) the election of each of the seven (7) director nominees set forth in the form of proxy; (ii) the ratification of the appointment of Plante & Moran, PLLC as the auditors of the Corporation for the 2023 fiscal year; and (iii) the approval of an advisory non-binding resolution approving the 2022 compensation of the named executive officers, as disclosed in this Proxy Statement.

Any revocation of a proxy must be delivered either to the principal executive office of the Corporation at any time up to and including the last business day preceding the day of the Meeting or any adjournment or postponement of the Meeting, or to the Chairman of the Board on the day of the Meeting, Tuesday, May 16, 2023, or any adjournment or postponement of the Meeting, prior to the time of the Meeting.

Notwithstanding the foregoing, shareholders must explicitly follow any instructions provided by their nominee.

PARTICULARS OF MATTERS TO BE ACTED UPON

PROPOSAL 1 - ELECTION OF DIRECTORS

Our Certificate of Incorporation (our “Charter”) provides that the Board shall consist of a total number of directors as determined from time to time exclusively by resolution adopted by the Board. The Board has determined that the number of directors constituting the Board currently be set at seven.

All director nominees are currently members of the Board and have been since the dates indicated in their respective profiles set forth below. It is contemplated that all of the nominees will be able to serve as directors; however, if a nominee should be unable to so serve for any reason prior to the Meeting, the persons named in the enclosed form of proxy reserve the right to vote for another nominee in their discretion. Each director elected will hold office until the next annual meeting of shareholders or until his/her successor is appointed and qualifies, unless his/her office is earlier vacated in accordance with the by-laws of the Corporation.

In order to be elected, a director nominee must receive a plurality of votes cast.

However, we have adopted a “Majority Election of Directors Policy” that provides that a director nominee who does not receive a majority (50% +1) of “FOR” votes cast at the Meeting in favor of his/her election in an uncontested election will be required to immediately submit his/her resignation to the Audit Committee and the resignation will be effective if/when accepted by the Board. The Audit Committee must make a recommendation to the Board to accept or reject the resignation, and the Board must act on the Audit Committee’s recommendation within 90 days of the Meeting. The Board shall accept the resignation absent extenuating circumstances. The Corporation will promptly issue a news release with the Board’s decision, and if the Board determines not to accept a resignation, the news release will state in full the reasons for that decision. A director who tenders a resignation pursuant to this policy will not participate in any meeting of the Board or any sub-committee of the Board at which the resignation is considered. A contested election is defined as a meeting at which the number of directors nominated for election is greater than the number of seats available on the Board.

Management and the Board unanimously recommend that shareholders vote FOR the election of all of the nominees whose names are set forth on the following pages. In the absence of contrary instructions, the persons designated by management of the Corporation in the enclosed form of proxy intend to vote FOR the election of all of the nominees whose names are set forth on the following pages.

Information set out below is as of March 22, 2023, unless otherwise indicated. Total compensation paid to the directors of the Corporation for the fiscal year ended December 31, 2022 is set out in the section entitled “Director Compensation” of the Proxy Statement.

Board of Directors and Director Nominees⁽¹⁾

Notes:

Executive Officers who are not Directors

Kent A. Hansen, 52, Executive Vice President and Chief Financial Officer. Mr. Hansen has served as CFO of the Corporation’s subsidiary, Kingsway America Inc., since December 2019 and Executive Vice President and CFO of the Corporation since February 2020. Prior to joining the Corporation, Mr. Hansen served as Chief Accounting Officer and Controller of LSC Communications, Inc. from 2016 to 2019. Prior to this, he served as Vice President, Assistant Controller, of Baxalta, Incorporated, a biopharmaceutical company from 2015 to 2016. Prior to this, he served in various finance and accounting roles from 2006 to 2015 with Scientific Games Corporation (formerly WMS Industries, Inc.), including Director of Accounting and SEC Reporting, Assistant Controller, and Group Chief Financial Officer. His earlier experience includes roles in accounting and financial reporting at Accenture and as an auditor at Ernst and Young LLP.

Involvement in Certain Legal Proceedings

Mr. Hannon was a director of Delhi Solac Inc., which was placed into bankruptcy on June 6, 2014.

Mr. Fitzgerald was a director of Hunter Licensed Sports Distributing Corporation (“Hunter”), which was the subject of a receivership order from the Superior Court of Quebec dated March 3, 2017. The receivership ended on September 27, 2017 following a Court order. Hunter was subsequently placed into bankruptcy on August 20, 2018.

In March of 2015, Mr. Stilwell and his affiliate, Stilwell Value LLC, an SEC-registered investment adviser (“Value”), consented to the entry of an administrative SEC order (the “Order”) that alleged civil violations of certain securities regulations for, among other things, failing to adequately disclose conflicts of interest presented by inter-fund loans between certain private investment partnerships managed by Value or Mr. Stilwell, which loans were repaid in full without monetary loss to investors from the alleged conduct. Under the Order, among other things, (1) Mr. Stilwell was suspended from March 2015 to March 2016 from association with Value or any other SEC-regulated investment business and paid a civil penalty of $100,000, and (2) Value paid a civil penalty of $250,000 and repaid certain management fees. All obligations under the Order have been fully discharged.

Mr. Hansen was a named executive officer of LSC Communications, Inc. until his departure from the company in 2019. LSC Communications was placed into bankruptcy in April 2020.

PROPOSAL 2 - APPOINTMENT OF AUDITORS

The Board recommends ratifying the appointment of Plante & Moran, PLLC (“Plante”) as the Corporation’s independent registered public accounting firm for the fiscal year ending December 31, 2023. Plante provides services in connection with the audit of the Corporation’s financial statements as well as assistance with our Annual Report on Form 10-K submitted to the SEC and consultation on matters relating to accounting and financial reporting. The audit committee of the Board expects to appoint Plante as the Corporation’s independent registered public accounting firm for the fiscal year ended December 31, 2023. Plante was the Corporation’s independent registered public accounting firm for the fiscal year ended December 31, 2022. Representatives of Plante are not expected to be present at the Meeting but will be available to respond to appropriate questions in writing.

In approving the selection of Plante as the Corporation’s independent registered public accounting firm for the year ended December 31, 2023, the Audit Committee considered existing and prior relationships between the Corporation and Plante and engaged in a dialogue with Plante regarding auditor independence issues. The Audit Committee determined that it was not aware of any relationships that could reasonably be expected to impact the objectivity or independence of Plante in performing audit services for the Corporation.

Audit Fees

The aggregate fees billed by Plante for professional services rendered for the audit of the consolidated financial statements of the Corporation and its subsidiaries, including expenses reimbursed, were $847,206 related to fiscal year 2022 and $793,175 related to fiscal year 2021.

Audit-Related Fees

The aggregate audit-related fees, including expenses reimbursed, billed by Plante for services rendered to the Corporation and its subsidiaries pertaining to the audit of the 401(k) plan were $14,100 in fiscal year 2022 and $13,500 for fiscal year 2021.

Tax Fees

The aggregate fees, including expenses reimbursed, billed by Plante for tax compliance, tax advice and tax planning services were zero in fiscal years 2022 and 2020.

All Other Fees

The aggregate fees, including expenses reimbursed, billed by Plante for services other than the services reported above under “Audit Fees,” “Audit-Related Fees” and “Taxes” were $141,378 related to due diligence assistance in fiscal year 2022 and $62,500 in fiscal year 2021.

The Audit Committee Charter provides for the Audit Committee to establish the auditors’ fees. Such fees have been based upon the complexity of the matters in question and the time incurred by the auditors. Management believes that the fees negotiated in the past with the auditors of the Corporation were reasonable in the circumstances and would be comparable to fees charged by other auditors providing similar services.

As discussed in the “Report of the Audit Committee” in the Proxy Statement, the Audit Committee has reviewed and considered whether the provision of services other than audit services is compatible with maintaining the auditors’ independence. The Audit Committee has considered and pre-approved expenditure limits for the Corporation’s auditors and established a system to review and pre-approve the provision of audit and non-audit services by the Corporation’s auditors to ensure they are consistent with maintaining the auditors’ independence. In each of the Corporation’s last two completed fiscal years and during the 2023 fiscal year to date, all audit and non-audit services were pre-approved by the Audit Committee.

Management and the Board unanimously recommend that shareholders vote FOR the ratification of the appointment of Plante as auditors of the Corporation for the fiscal year ending December 31, 2023. In the absence of contrary instructions, the persons designated by management of the Corporation in the enclosed form of proxy intend to vote FOR the ratification of Plante as auditors of the Corporation for the fiscal year ending December 31, 2023.

PROPOSAL 3 - ADVISORY VOTE TO APPROVE THE COMPENSATION OF THE NAMED EXECUTIVE OFFICERS

The Corporation is providing shareholders the opportunity to vote on a non-binding, advisory basis to approve the compensation of the named executive officers, commonly known as a “say-on-pay” vote, as required by Section 14A of the Exchange Act.

At the 2018 annual meeting, shareholders were asked to cast a non-binding advisory vote on whether the say-on-pay vote should be held every year, every two years, or every three years. A majority of shareholders voting on the matter indicated a preference for holding the say-on-pay vote on an annual basis in accordance with the recommendation of

the Board. Accordingly, the Board determined that the non-binding advisory vote to approve the compensation of our named executive officers was to be held on an annual basis, at least until the next non-binding shareholder vote on the frequency with which future say-on-pay votes should be held which shall be in 2024.

Resolution

The advisory vote on executive compensation is a non-binding vote on the compensation of the Corporation’s named executive officers, as described in “Compensation of Executive Officers and Directors” below. Shareholders may abstain from voting, if they so choose. Accordingly, the Corporation is asking its shareholders to approve the following resolution at the Meeting:

RESOLVED that the compensation paid to the Corporation’s named executive officers, including the compensation tables contained in the Proxy Statement dated April 6, 2023, be and is hereby approved.

As an advisory vote, the result of the say-on-pay vote is non-binding on the Corporation and the Board; however, the Board and the Compensation & Management Resources Committee value the opinions of shareholders and will consider the outcome of the vote when making future compensation decisions for our named executive officers.

Management and the Board unanimously recommend that shareholders vote FOR the approval of the advisory resolution approving the 2022 compensation of the named executive officers, as disclosed in the Proxy Statement. In the absence of contrary instructions, the persons designated by management of the Corporation in the enclosed form of proxy intend to vote FOR the approval of the advisory resolution approving the 2022 compensation of the named executive officers.

CORPORATE GOVERNANCE MATTERS

Corporate Governance Guidelines and Code of Business Conduct & Ethics

Except for Mr. Fitzgerald, the Corporation’s President and Chief Executive Officer, the current and proposed directors are independent as determined in accordance with Section 301 of SOX and the criteria for independence established by the NYSE. Accordingly, the majority of the current and proposed directors are independent.

During 2022, the Board met nine (9) times, including in-person and telephonic meetings. Each director attended at least 75% of the total meetings of the Board and committees of the Board on which he or she served. Additionally, the directors often communicate with one another and with management informally to discuss our affairs.

The Corporation has adopted Corporate Governance Guidelines which comply with the NYSE listing standards and corporate governance requirements of applicable law. The Corporate Governance Guidelines were amended and adopted by the Board on May 23, 2019 and are periodically reviewed. The Corporate Governance Guidelines can be found on the Corporation’s website at www.kingsway-financial.com/corporate-governance.

The Corporation has also adopted a written code of ethics, which was amended and adopted by the Audit Committee on March 2, 2022, applicable to our directors, principal executive officer, principal financial officer, and other senior financial personnel. The Code of Business Conduct & Ethics is posted on the Corporation’s website at www.kingsway-financial.com/corporate-governance. Any future amendments to the Corporation’s code of ethics for senior financial personnel and any grant of waiver from a provision of the code requiring disclosure under applicable SEC rules will be disclosed in the “Corporate Governance” section of our website. The Corporation will provide to any person, without charge, a copy of the code of ethics, upon written request to the Corporation, Attention: Chief Financial Officer, 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606.

Securities Trading Policy

The Corporation has adopted a securities trading policy that prohibits directors, officers, employees and certain other covered persons from engaging in insider trading and from entering into hedging or monetization transactions or similar arrangements with respect to the Corporation’s securities. The Disclosure, Securities Trading and Confidentiality Policy is posted on the Corporation’s website at www.kingsway-financial.com/corporate-governance.

Board Committees

The board has four (4) standing committees: the Audit Committee, the Compensation & Management Resources Committee, the Nominating and Corporate Governance Committee, and the Investment Committee.

Audit Committee

The Board has a standing Audit Committee which operates pursuant to a written charter adopted by the Board. The Audit Committee consists of three or more directors, each of whom is an outside director who is unrelated to the Corporation, free from any relationship that would interfere with the exercise of his or her independent judgment and each of whom is “independent” under the listing rules of the NYSE. Audit Committee members meet the requirements of all applicable securities laws and the NYSE. All members of the Audit Committee are financially literate, being defined as able to read and understand basic financial statements, and the Chair of the Audit Committee has accounting or related financial management expertise. At least one member of the Audit Committee is an “audit committee financial expert” as defined in the rules and regulations of the SEC. Pursuant to the Audit Committee Charter, members of the Audit Committee may not simultaneously serve on the audit committees of more than two other public companies without the approval of the Audit Committee.

The primary purpose of the Audit Committee is to:

As of April 6, 2023, the Audit Committee was comprised of Gregory P. Hannon (Chair), Charles Frischer and Corissa B. Porcelli. The Board has determined that each member of the Audit Committee is “independent” and meets the financial literacy requirements of the NYSE listing standards, and that each member of the Audit Committee meets the enhanced independence standards established by the SEC (including Section 10A(m)(3) of and Rule 10A-3 under the Exchange Act). The Board has determined that Mr. Hannon qualifies as an “audit committee financial expert” as that term is defined in the rules and regulations established by the SEC.

The Audit Committee held four (4) meetings, including telephonic meetings, in the fiscal year ended December 31, 2022. The responsibilities and duties of the Audit Committee are set out in the Audit Committee’s charter, which was amended and adopted by the Board on May 23, 2019 and is available in the “Corporate Governance” section of the Corporation’s website at www.kingsway-financial.com/corporate-governance.

Report of the Audit Committee

The Audit Committee has met and held discussions with management and the independent auditors. Management represented to the Audit Committee that the Corporation’s consolidated financial statements were prepared in accordance with accounting principles generally accepted in the United States of America, and the Audit Committee has reviewed and discussed the audited consolidated financial statements with management and the independent auditors. The Audit Committee discussed with the independent auditors the matters required to be discussed by the applicable requirements of the Public Company Accounting Oversight Board (“PCAOB”) and the SEC.

The Corporation’s independent auditors also provided to the Audit Committee the written disclosures required by applicable requirements of the PCAOB regarding the independent auditors’ communications with the Audit Committee concerning independence, and the Audit Committee discussed with the independent auditors that firm’s independence. The Audit Committee also considered whether the provision of non-audit services by the independent auditors is compatible with their independence.

Based upon the Audit Committee’s discussion with management and the Corporation’s independent auditors and the Audit Committee’s review of the representation of management and the report of the independent auditors to the Audit Committee, the Audit Committee recommended that the Board include the audited consolidated financial statements in the Corporation’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022 filed with the SEC.

Members of the Audit Committee

Gregory P. Hannon (Chair)

Charles Frischer

Corissa B. Porcelli

Compensation & Management Resources Committee

The Board has a standing Compensation & Management Resources Committee (the “Compensation Committee”) which operates pursuant to a written charter adopted by the Board. The Compensation Committee consists of two or more directors, each of whom must satisfy the applicable independence requirements of the New York Stock Exchange and any other regulatory authorities. At least two members of the Committee also must qualify as “non-employee” directors within the meaning of Rule 16b-3 under the Securities Exchange Act of 1934, as amended. The Board has determined that each member of the Compensation Committee in the fiscal year ended December 31, 2022 was independent under the criteria established by the applicable regulatory authorities.

The Compensation Committee held three (3) telephonic meetings in the fiscal year ended December 31, 2022. The responsibilities and duties of the Compensation Committee are set out in the Compensation Committee’s Charter, which was amended and adopted by the Board on May 23, 2019 and is available in the “Corporate Governance” section of the Corporation’s website at www.kingsway-financial.com/corporate-governance.

The primary purpose of the Compensation Committee is to:

In making its compensation decisions and recommendations, the Compensation Committee may take into account the recommendations of the Chief Executive Officer with respect to the other senior officers of the Corporation and the President of each of the Corporation’s subsidiaries. Other than giving such recommendations, however, the Chief Executive Officer has no formal role and no authority to determine the amount or form of executive and director compensation.

The Compensation Committee has the sole authority to retain and terminate (or obtain the advice of) any adviser to assist it in the performance of its duties, but only after taking into consideration all factors relevant to the adviser’s independence from management, including those specified in Section 303A.05(c)(iv) of the New York Stock Exchange Listed Company Manual. The Compensation Committee shall evaluate and determine whether any compensation consultant retained or to be retained by it has any conflict of interest in accordance with Item 407(e)(3)(iv) of Regulation S-K under the rules and regulations of the SEC. As currently constituted, the Compensation Committee has never engaged a compensation consultant nor does it have any current plans to do so.

As of April 6, 2023, the Compensation Committee was comprised of Joseph D. Stilwell (Chair) and Terence M. Kavanagh.

Nominating and Corporate Governance Committee

The Board has a standing Nominating and Corporate Governance Committee which operates pursuant to a written charter adopted by the Board. The Nominating and Corporate Governance Committee consists of no fewer than two directors, each of whom satisfies the applicable independence requirements of the New York Stock Exchange and any other regulatory requirements. The Board has determined that each member of the Nominating and Corporate Governance Committee in the fiscal year ended December 31, 2022 was independent under the criteria established by the applicable regulatory authorities.

The Nominating and Corporate Governance Committee held one (1) telephonic meeting in the fiscal year ended December 31, 2022. The responsibilities and duties of the Nominating and Corporate Governance Committee are set out in the Nominating and Corporate Governance Committee’s Charter, which was amended and adopted by the Board on May 23, 2019 and is available in the “Corporate Governance” section of the Corporation’s website at www.kingsway-financial.com/corporate-governance. 

The primary purpose of the Nominating and Corporate Governance Committee is to:

The Corporation believes that the current Board has the mix of industry knowledge, experience and financial expertise required to provide strong oversight of the Corporation. The Corporation does not have a diversity policy. In considering a candidate for nomination as a member of the Board, the Nominating and Corporate Governance Committee will consider criteria such as equity ownership; an entrepreneurial mindset; independence; occupational background; level and type of business experience; and the number of boards on which the individual serves. The Nominating and Corporate Governance Committee does not take into account race, sex or creed in its evaluation of any director or nominee.

The Nominating and Corporate Governance Committee will consider recommendations for director candidates submitted by shareholders in the same manner as consideration of candidates recommended by outside search firms,

incumbent directors and others. Any such recommendation should be submitted in writing to the Nominating and Corporate Governance Committee in care of the Office of the Chief Financial Officer at 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606.

As of April 6, 2023, the Nominating and Corporate Governance Committee was comprised of Gregory P. Hannon (Chair) and Joseph D. Stilwell.

Investment Committee

The Board has a standing Investment Committee which operates pursuant to a written charter adopted by the Board. The Investment Committee consists of two or more directors, the majority of whom must satisfy the applicable independence requirements of the applicable regulatory authorities. The Board has determined that each member of the Investment Committee in the fiscal year ended December 31, 2022 was independent under the criteria established by the applicable regulatory authorities.

The Investment Committee did not hold a meeting in the fiscal year ended December 31, 2022. The responsibilities and duties of the Investment Committee are set out in the Investment Committee’s charter, which was amended and adopted by the Board on May 23, 2019 and is available in the “Corporate Governance” section of the Corporation’s website at www.kingsway-financial.com/corporate-governance.

The primary purpose of the Investment Committee is to:

As of April 7, 2023, the Investment Committee was comprised of Douglas Levine (Chair), Joseph D. Stilwell and Terence M. Kavanagh.

Communications with the Board

It is the Corporation’s policy to forward to the directors any correspondence it receives that is addressed to them. Shareholders, or other interested parties, who wish to communicate with the directors may do so by sending their correspondence addressed to the director or directors as follows: Kingsway Financial Services Inc., Attention: Investor Relations, 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606.

Our directors’ attendance at annual meetings can provide shareholders with an opportunity to communicate with directors about issues affecting the Corporation. Our Corporate Governance Guidelines encourage our directors to attend the annual meeting of shareholders. All of the directors then in office attended the 2022 annual meeting of shareholders.

Board Leadership Structure and Role in Risk Oversight

Our President and Chief Executive Officer, John T. Fitzgerald, joined our Board on April 21, 2016. Since September 16, 2013, Terence M. Kavanagh has been serving as our independent, non-executive Chairman of the Board. The Chairman focuses on the overall strategy of the business and leadership of the Board, including: presiding at all Board meetings, at all executive sessions of the Board held without management and at the annual meeting of shareholders; establishing Board meeting agendas in consultation with the Chairs of the Board committees; acting as a liaison between the directors

and the Corporation’s management; advising the Chief Executive Officer of the quality, quantity and timeliness of the flow of information from management to enable the directors to effectively and responsibly perform their duties; facilitating communication among directors; and maintaining frequent contact with the Chief Executive Officer.

The Board believes that its optimal leadership structure may vary as circumstances warrant and views its current structure as appropriate to supervise the business and affairs of the Corporation.

The Corporation’s management is primarily responsible for managing risk and informing the Board of the material risks confronting the Corporation. The Board has oversight responsibility of the processes established to monitor and manage such risks. The Board believes that such oversight function is the responsibility of the entire Board through frequent reports and discussions at regularly scheduled Board meetings. In addition, the Board has delegated specific risk management oversight responsibility to the Audit Committee and to the independent members of the Board. In particular, the Audit Committee oversees the management of risks related to accounting, auditing and financial reporting and maintaining effective internal controls for financial reporting. The independent members of the Board oversee risk management related to the Corporation’s corporate governance practices and the Corporation’s executive compensation plans and arrangements. These specific risk categories and the Corporation’s risk management practices are regularly reviewed by the entire Board in the ordinary course of regular Board meetings.

COMPENSATION OF EXECUTIVE OFFICERS AND DIRECTORS

Named Executive Officers for 2022

The following individuals are the Corporation’s named executive officers for 2022. Each of the following individuals held the position(s) set forth opposite his name as of December 31, 2022.

Notes:

2022 Summary Compensation Table

The following table provides information regarding the compensation of our named executive officers for the last two completed fiscal years.

Notes:

2022 Pay Versus Performance

The following table sets forth information concerning: (1) the compensation of our Chief Executive Officer and President, John T. Fitzgerald and the average compensation for our other named executive officer, Kent A. Hansen, both as reported in the Summary Compensation Table and with certain adjustments to reflect the “compensation actually paid” ("CAP") to such individuals, as defined under SEC rules, for each of the fiscal years ended December 31, 2021 and 2022 and (2) our total shareholder return (“TSR”) and Net Income over such years in accordance with SEC rules:

(1) Mr. Fitzgerald was the Principal Executive Officer (“PEO”) in 2022 and 2021.

(2) Mr. Hansen was the only Non-PEO Named Executive Officer (“NEO”) in 2022 and 2021.

Officer compensation is determined by the Compensation Committee. In terms of base salary the Compensation Committee considers the market for similarly situated employees at peer companies and the employee’s overall performance both individually and as it relates to the overall results. Variable compensation considers profitability during the year. Compensation actually paid to the PEO and Non-PEO NEO in 2022 and 2021 were based upon 2022 and 2021financial results, as well as the achievement of strategic objectives. The Compensation Committee also considered shareholder return as a factor in compensation, given the steady increase in our share price over the past few years.

2022 Outstanding Equity Awards at Fiscal Year-End

Notes:

Potential Payments Upon Termination or Change in Control

The Corporation maintains a severance policy (the “Severance Policy”) for the payment of certain benefits to certain eligible employees of the Corporation, but not our named executive officers. Benefits are paid under the Severance Policy following a termination of employment in connection with a reduction in work force. Under the Severance Policy, upon a qualifying termination of employment, the named executive officers are entitled to two weeks of severance pay for each full year of service with the Corporation, with a minimum of 12 weeks of severance pay and a maximum of 39 weeks of severance pay. Participants are also entitled to receive subsidized benefits as provided under the Consolidated Omnibus Budget Reconciliation Act during the severance period.

In lieu of benefits under the Severance Policy, Mr. Fitzgerald is entitled to receive severance benefits under an individual severance agreement consisting of 12 months of base salary, paid in a lump sum, upon either (x) a termination of employment by the Corporation, other than for “Cause,” or (y) Mr. Fitzgerald’s resignation as a result of a “Constructive Termination,” subject, in each case, to Mr. Fitzgerald’s execution of a release of claims. In addition, upon a termination without “Cause,” a resignation by Mr. Fitzgerald as a result of a “Constructive Termination,” Mr. Fitzgerald’s death or disability, or Mr. Fitzgerald’s “constructive resignation,” Mr. Fitzgerald would be entitled to accelerated vesting of a prorated portion of his 2018 restricted stock award (as described in footnote 3 to the “2022 Outstanding Awards at Fiscal Year-End Table,” above). Mr. Fitzgerald’s 2018 restricted stock award is also subject to accelerated vesting upon a “change in control.” As defined in Mr. Fitzgerald’s severance agreement, (A) “Cause” means Mr. Fitzgerald’s involuntary termination due to: (i) an intentional act of fraud, embezzlement, theft, or any other illegal act against the Corporation, any of which would constitute a felony; (ii) Mr. Fitzgerald’s improper disclosure or use of the Corporation’s confidential information but only where the Corporation has established that such disclosure or use has financially and materially injured the Corporation; or (iii) a material breach of Mr. Fitzgerald’s duty of loyalty to the Corporation but only where the Corporation has established that such breach has financially and materially injured the Corporation, (B) “Constructive Termination” means Mr. Fitzgerald’s voluntary resignation within 45 days following written notice to each independent member of the Board setting forth in reasonable detail the occurrence of any of the following events without Mr. Fitzgerald’s written consent that is not cured by the Corporation within 30 days after such notice: (i) any

material diminution in job duties and responsibilities or the imposition of job requirements materially inconsistent with Mr. Fitzgerald’s position with the Corporation; (ii) a reduction in Mr. Fitzgerald’s then-current base salary, other than an across-the-board reduction of no more than 10% in the base salary of all executive level employees; (iii) a material reduction in Mr. Fitzgerald’s annual incentive compensation opportunities; or (iv) Mr. Fitzgerald has established that he has been subject to a hostile work environment, and (C) “Constructive Resignation” means a voluntary termination of employment by the Corporation as a result of Mr. Fitzgerald’s habitual neglect or gross negligence in the performance of Mr. Fitzgerald’s duties and responsibilities that has a material adverse effect on the business or financial condition of the Corporation, after written notice from the board setting forth the facts in reasonable detail constituting habitual neglect or gross negligence that Mr. Fitzgerald does not cure within thirty (30) days of such notice.

In lieu of any severance benefits under the Severance Policy, Mr. Hansen’s offer letter instead provides that he is entitled to receive severance benefits of a lump sum payment equal to 100% of his then-current base salary for a termination of employment by the Corporation, other than a termination for “cause,” subject to Mr. Hansen’s execution of a release of claims.

Director Compensation

Narrative Description

The Corporation’s director compensation program is designed to provide reasonable compensation for the risks and responsibilities of being a director. Only non-employee directors of the Board are remunerated for serving as directors of the Corporation. Non-employee directors received a single retainer fee, payable in quarterly installments in advance, in the amount of $80,000. The Chairmen of the Board and the Audit Committee each receive an additional $40,000 annually, also payable in quarterly installments in advance.

2022 Director Compensation

The following table provides information regarding the compensation of our non-employee directors for 2022.

Notes:

Securities Authorized for Issuance Under Equity Compensation Plans

The following table sets forth information regarding the securities authorized for issuance under our equity compensation plans as of December 31, 2022, the end of our last fiscal year:

CERTAIN RELATIONSHIPS AND TRANSACTIONS WITH RELATED PERSONS

Other than as set forth below, no director, executive officer or person who is a proposed nominee for election as a director of the Corporation, and no associate or affiliate of any such director, executive officer or proposed nominee, nor, to the best knowledge of the directors and executive officers of the Corporation after having made reasonable inquiry, any person or company who beneficially owns, controls or directs, directly or indirectly, voting securities of the Corporation carrying more than five (5%) percent of the voting rights attached to all outstanding voting securities of the Corporation at the date hereof, or any associate or affiliate thereof, has any material interest, direct or indirect, in any transaction since the commencement of the Corporation’s most recently completed fiscal year or in any proposed transaction which has materially affected or would materially affect the Corporation or any of its subsidiaries which is in excess of the lesser of $120,000 or 1% of the average of the Corporation’s total assets at year-end for the last three completed fiscal years.

As previously disclosed, the Corporation acquired Argo Management Group, LLC (“Argo”) in April 2016. Argo’s primary business is to act as Managing Member of Argo Holdings Fund I, LLC (the “Fund”). As of the date of this Proxy Statement, each of the Corporation, Mr. Fitzgerald, and certain of Mr. Fitzgerald’s immediate family members own equity interests in the Fund, which interests were acquired prior to the acquisition of Argo. During the fiscal year ended December 31, 2022: (a) the Corporation received $447,826 in distributions from the Fund; (b) Mr. Fitzgerald received $111,957 in distributions from the Fund; and (c) two of Mr. Fitzgerald’s immediate family members, who are investors in the Fund, each received $55,978 in distributions from the Fund.

OTHER MATTERS

As of the date of the Proxy Statement, management and the Board know of no amendment, variation or other matter expected to come before the Meeting other than the matters referred to in the Notice of Meeting; however, if any other matter properly comes before the Meeting, the persons named in the accompanying form of proxy will vote on such matter in accordance with their best judgment.

HOUSEHOLDING OF PROXY MATERIALS

The SEC has adopted rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery requirements for annual meeting materials with respect to two or more shareholders sharing the same address by delivering a single set of annual meeting materials addressed to those shareholders. This process, which is commonly referred to as “householding,” potentially means extra convenience for shareholders and cost savings for companies.

This year, a number of brokers with account holders who are our shareholders will be “householding” our proxy materials. A single set of annual meeting materials will be delivered to multiple shareholders sharing an address unless contrary instructions have been received from the affected shareholders. Once you have received notice from your broker that they will be “householding” communications to your address, “householding” will continue until you are notified otherwise or until you revoke your consent. We will deliver promptly upon written or oral request a separate set of annual meeting materials to any shareholder who received these materials at a shared address. If, at any time, you no longer wish to participate in “householding” and would prefer to receive a separate set of annual meeting materials, please notify your broker or us. Direct your written request to Kingsway Financial Services Inc., Attention: Investor Relations, 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606, or call646-415-8972. Shareholders who currently receive multiple copies of the annual meeting materials at their addresses and would like to request “householding” of their communications should contact their brokers.

ANNUAL REPORT

Copies of the Annual Report on Form 10-K and all amendments thereto (including financial statements and financial statement schedules) may be obtained without charge by writing to Kingsway Financial Services Inc., Attention: Investor Relations, 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606. A request for a copy of the Annual Report on Form 10-K and any amendments thereto must set forth a good-faith representation that the requesting party was either a holder of record or a beneficial owner of Common Shares on the Record Date. Exhibits to the Annual Report on Form 10-K, and any amendments thereto, will be mailed upon similar request.

SHAREHOLDER PROPOSALS FOR 2024 ANNUAL MEETING

All proposals of shareholders intended to be included in the Proxy Statement relating to the 2024 annual meeting must be received by the Corporation at our principal executive office not less than 120 calendar days before the first anniversary of the date of the Corporation’s proxy statement released to shareholders in connection with the 2023 annual meeting (which would be December 8, 2023). If the date of the 2024 annual meeting is changed by more than 30 days from the date of the first anniversary of the 2023 annual meeting, then the deadline for submission pursuant to Rule 14a-8 under the Exchange Act (“Rule 14a-8”) is a reasonable time before we begin to print and send the proxy statement for the 2024 annual meeting. All such proposals must comply with the requirements of Rule 14a-8, which sets forth specific requirements and limitations applicable to nominations and proposals at annual meetings of shareholders and should be sent to Kingsway Financial Services Inc., Attention: Investor Relations, 10 S. Riverside Plaza, Suite 1520, Chicago IL 60606. In order for shareholders to give timely notice of nominations for directors for inclusion on a universal proxy card in connection with the 2024 Annual Meeting, notice must be submitted by the same deadline as disclosed above under the advance notice provisions of our Bylaws and must include the information in the notice required by our Bylaws and by Rule 14a-19(b)(2) and Rule 14a-19(b)(3) under the Exchange Act.

Under our by-laws and applicable Delaware law, if a shareholder intends to nominate a person for election to the Board of Directors or present a proposal at the 2024 annual meeting, but does not intend to include such proposal in the Corporation’s proxy statement, then such nomination or proposal must be in writing and received by the Secretary of the Corporation at the principal executive offices of the Corporation no less than ninety (90) days (which would be February 16, 2024) nor more than one hundred and twenty (120) days (which would be January 17, 2024) prior to the first anniversary of the 2023 annual meeting May 16, 2024. In the event that the date of the 2024 annual meeting is advanced by more than thirty (30) days, or delayed by more than seventy (70) days, from the anniversary date of the 2023 annual meeting, notice by the stockholder to be timely must be received not earlier than one hundred and twenty (120) days prior to such annual meeting and not later than the close of business on the later of the ninetieth (90th) day prior to such annual meeting or the tenth (10th) day following the day on which public announcement of the date of such meeting is first made.

The persons named in the Corporation’s form of proxy for the 2024 annual meeting will have discretionary authority to vote the shares represented by such proxies on the shareholder proposal, without including information about the proposal in the Corporation’s proxy materials.

With respect to business to be brought before the Meeting, we have not received any notices from shareholders that we were required to include in the Proxy Statement.

ADDITIONAL INFORMATION

Financial information about the Corporation is contained in its consolidated financial statements and Management’s Discussion and Analysis for the fiscal year ended December 31, 2022, and additional information relating to the Corporation is on EDGAR at www.sec.gov, or on SEDAR at www.sedar.com. If you would like to obtain, at no cost to you, a copy of any of the following documents:

please send your request to:

Kingsway Financial Services Inc.

Attention: Investor Relations

10 S. Riverside Plaza, Suite 1520

Chicago IL 60606

The Board has approved the contents of the Proxy Statement and the sending of it to the directors, the shareholders, and the auditors of the Corporation.

DATED this April 6, 2023.

Your vote matters – here’s how to vote! You may vote online or by phone instead of mailing this card. Online Go to www.investorvote.com/KFS or scan the QR code — login details are located in the shaded bar below. Using a black ink pen, mark your votes with an X as shown in this example. Please do not write outside the designated areas. Phone Call toll free 1-800-652-VOTE (8683) within the USA, US territories and Canada Save paper, time and money! Sign up for electronic delivery at www.investorvote.com/KFS 2023 Annual Meeting Proxy Card q IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE. q A Proposals — The Board of Directors recommend a vote FOR all the nominees listed and FOR Proposals 2 and 3. For Withhold For Withhold For Withhold + 1. To elect seven (7) directors of the Corporation to hold office for a term of one (1) year or until their successors are duly appointed and qualified; 01 - John T. Fitzgerald 04 - Terence M. Kavanagh 02 - Charles Frischer 05 - Douglas Levine 03 - Gregory P. Hannon 06 - Corissa B. Porcelli 07 - Joseph D. Stilwell 2. To ratify the appointment of Plante & Moran, PLLC as the auditors of the Corporation for the fiscal year ending December 31, 2023; and For Against Abstain 3. To approve, on a non-binding and advisory basis, the compensation of the named executive officers of the Corporation (say-on-pay). For Against Abstain B Authorized Signatures — This section must be completed for your vote to count. Please date and sign below. Please sign exactly as name(s) appears hereon. Joint owners should each sign. When signing as attorney, executor, administrator, corporate officer, trustee, guardian, or custodian, please give full title. Date (mm/dd/yyyy) — Please print date below. Signature 1 — Please keep signature within the box. Signature 2 — Please keep signature within the box. 03SADC 7 2 B V +

2023 Annual Meeting of Kingsway Financial Services Inc. Shareholders The 2023 Annual Meeting of Shareholders of Kingsway Financial Services Inc will be held on May 16, 2023 at 8:00 am CT (9:00 am ET), virtually via the Internet at meetnow.global/MZVHWJG and in person at New York Stock Exchange, Hamilton Room, 11 Wall St, New York, NY 10005 To access the virtual meeting, you must have the information that is printed in the shaded bar located on the reverse side of this form. Important notice regarding the Internet availability of proxy materials for the Annual Meeting of Shareholders. The material is available at: www.investorvote.com/KFS Small steps make an impact. Help the environment by consenting to receive electronic delivery, sign up at www.investorvote.com/KFS q IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE. q Kingsway Financial Services Inc. + Notice of 2023 Annual Meeting of Shareholders Proxy Solicited by Board of Directors for Annual Meeting — May 16, 2023 Terence M. Kavanagh, Chairman of the Board, or, failing him, John T. Fitzgerald, President and Chief Executive Officer, or either of them, each with the power of substitution, are hereby authorized to represent and vote the shares of the undersigned, with all the powers which the undersigned would possess if personally present, at the Annual Meeting of Shareholders of Kingsway Financial Services Inc. to be held on May 16, 2023 or at any postponement or adjournment thereof. Shares represented by this proxy will be voted by the shareholder. If no such directions are indicated, the Proxies will have authority to vote FOR the election of the Board of Directors and FOR items 2 and 3. In their discretion, the Proxies are authorized to vote upon such other business as may properly come before the meeting. (Items to be voted appear on reverse side) C Non-Voting Items Change of Address — Please print new address below. Comments — Please print your comments below. +