KFS / Kingsway Financial Services Inc. - Depositi SEC, Relazione annuale, dichiarazione di delega

Kingsway Financial Services Inc.
US ˙ NYSE ˙ US4969042021

Statistiche di base
CIK 1072627
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Kingsway Financial Services Inc.
SEC Filings (Chronological Order)
Questa pagina fornisce un elenco completo e cronologico dei depositi SEC, esclusi i documenti di proprietà che forniamo altrove.
September 5, 2025 424B3

Kingsway Financial Services Inc. Up to 1,419,001 Shares of Common Stock

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No. 333 – 289859 Kingsway Financial Services Inc. Up to 1,419,001 Shares of Common Stock This prospectus relates to the resale by the selling stockholders named herein or their permitted transferees (the “Selling Stockholders”) of up to 1,419,001 shares of our common stock, par value $0.01 per share (the “common stock”), including up to (i)

August 26, 2025 S-1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter)

Table of Contents As filed with the U.S. Securities and Exchange Commission on August 26, 2025 Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or

August 26, 2025 EX-FILING FEES

Security Type

Calculation of Filing Fee Tables S-1 KINGSWAY FINANCIAL SERVICES INC Table 1: Newly Registered and Carry Forward Securities ☐Not Applicable Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry Forward Form Type Carry Forward File Number Carry Forward Initial Effective Date Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to be Paid 1 Equity common stock, $0.

August 7, 2025 EX-99.1

KINGSWAY REPORTS Second QUARTER 2025 FINANCIAL RESULTS Management to Host Conference Call Today, August 7, 2025, at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS Second QUARTER 2025 FINANCIAL RESULTS Management to Host Conference Call Today, August 7, 2025, at 5 p.m. ET Chicago - August 7, 2025 - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”), the only publicly-traded US company employing the Search Fund model to acquire and build great businesses, today announced its operating results for the three

August 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

August 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 7, 2025 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 7, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

July 7, 2025 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 1, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

July 7, 2025 EX-10.2

Credit Agreement, dated July 1, 2025, by and between Roundhouse Electric & Equipment Co., Inc., Longhorns Acquisition LLC and Main Street Bank.*

Exhibit 10.2 CREDIT AGREEMENT This Credit Agreement (this “Agreement”) is made as of the 1st day of July, 2025 by and between Roundhouse Electric & Equipment & Co., Inc., a Texas Corporation (“Roundhouse”), having an address at 2224 South Grandview Avenue, Odessa, Texas, 79766, Longhorns Acquisition LLC, a Delaware limited liability company (“Longhorns”), having an address at 10 South Riverside Pl

July 7, 2025 EX-10.1

Stock Purchase Agreement, dated July 1, 2025, by and among Longhorns Acquisition LLC, Armando Gonzales and Lee Hudson.*

Exhibit 10.1 STOCK PURCHASE AGREEMENT BY AND AMONG LONGHORNS ACQUISITION LLC, AS BUYER, AND ARMANDO GONZALES AND LEE HUDSON, AS SELLERS Dated as of July 1, 2025 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS 1 ARTICLE II PURCHASE AND SALE 13 Section 2.1 Purchase and Sale 13 Section 2.2 Purchase Price Adjustment 14 ARTICLE III CLOSING 16 Section 3.1 Closing 16 Section 3.2 Closing Deliveries of Seller

June 25, 2025 EX-99.1

KINGSWAY ANNOUNCES $15.7 MILLION PIPE TO ACCELERATE GROWTH KSX Guidance Increased From 2-3 Acquisitions Per Year To 3-5 Acquisitions Per Year

Exhibit 99.1 KINGSWAY ANNOUNCES $15.7 MILLION PIPE TO ACCELERATE GROWTH KSX Guidance Increased From 2-3 Acquisitions Per Year To 3-5 Acquisitions Per Year Chicago – June 24, 2025 – (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”), the only publicly-traded US company employing the Search Fund model to acquire and build great businesses, today announced the closing of a $15

June 25, 2025 EX-10.1

Stock Purchase Agreement, dated June 24, 2025, by and among the Company and the purchasers named therein.

Exhibit 10.1 EXECUTION VERSION STOCK PURCHASE AGREEMENT This Stock Purchase Agreement (this “Agreement”) is dated as of June 24, 2025 (the “Effective Date”), by and among Kingsway Financial Services, Inc., a Delaware corporation (the “Company”), and each of those persons and entities, severally and not jointly, listed as a Purchaser on the Schedule of Purchasers attached as Exhibit A hereto (the “

June 25, 2025 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 24, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

May 21, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 19, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 19, 2025 EX-10.1

Form of Subscription Agreement – Legal Entity

Exhibit 10.1 Execution Version SUBSCRIPTION AGREEMENT – LEGAL ENTITY This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of May , 2025 by and between , a (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption from securities reg

May 19, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

-12-31 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware 001-15204 85-1792291 (State or other jurisdiction of incorporation)

May 19, 2025 EX-10.2

Form of Subscription Agreement – Individual Investor

Exhibit 10.2 Execution Version SUBSCRIPTION AGREEMENT - INDIVIDUAL This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of May [X], 2025 by and between , a resident of (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption from s

May 19, 2025 EX-3.1

Class D Certificate of Designations

Exhibit 3.1 Execution Version KINGSWAY FINANCIAL SERVICES INC. CERTIFICATE OF DESIGNATIONS OF CLASS D PREFERRED STOCK Pursuant to Section 151 of the Delaware General Corporation Law (as amended, supplemented or restated from time to time, the “DGCL”), Kingsway Financial Services Inc., a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), in accordance wi

May 19, 2025 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 19, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 8, 2025 EX-99.1

KINGSWAY REPORTS First QUARTER 2025 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS First QUARTER 2025 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago - May 8, 2025 - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”), the only publicly-traded US company employing the Search Fund model to acquire and build great businesses, today announced its operating results for the three months ended March 3

May 8, 2025 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 8, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 8, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

April 15, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 11, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware 001-15204 85-1792291 (State or other jurisdiction (Commission (IRS Empl

April 9, 2025 DEFA14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

April 9, 2025 DEF 14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

April 2, 2025 EX-99.1

KINGSWAY FINANCIAL SERVICES INC. APPOINTS ADAM J. PATINKIN AND JOSHUA S. HOROWITZ TO ITS BOARD OF DIRECTORS

Exhibit 99.1 KINGSWAY FINANCIAL SERVICES INC. APPOINTS ADAM J. PATINKIN AND JOSHUA S. HOROWITZ TO ITS BOARD OF DIRECTORS Chicago - (Marh 31, 2025) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced it has appointed Adam J. Patinkin and Joshua S. Horowitz to its Board of Directors. The Company has also agreed to nominate Mr. Patinkin and Mr. Horowitz for el

April 2, 2025 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 31, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation) 001-15204 (Commission Fi

March 17, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

March 17, 2025 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware Kingsway General Insurance Company Ontario Red Shield (Barbados) Inc. Barbados Kingsway America Inc. Delaware Ravix Acquisition LLC Delaware Ravix Group, Inc Delaware CSuite Financial Partners, LLC California Argo Management Group, LLC Delaware Argo

March 17, 2025 EX-19

Disclosure, Securities Trading and Confidentiality Policy.

Exhibit 19 Disclosure, Securities Trading and Confidentiality Policy Purpose The purpose of this Policy is to provide directors, officers, employees and others considered to have a special relationship1 with Kingsway direction on: (a) the process and restrictions for public disclosure made by Kingsway Financial Services Inc.

March 17, 2025 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 17, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) (Commission File Number) 001-15204 Delaware (State or Other Jurisdiction of Inco

March 17, 2025 EX-99.1

KINGSWAY REPORTS FULL YEAR 2024 FINANCIAL RESULTS Management to Host Conference Call Tuesday, March 18, 2025, at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS FULL YEAR 2024 FINANCIAL RESULTS Management to Host Conference Call Tuesday, March 18, 2025, at 5 p.m. ET Chicago - (March 17, 2025) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the 12 months ended December 31, 2024. Full Year 2024 Consolidated Financial Highlights ● Consolidated revenue increas

February 24, 2025 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 18, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware 001-15204 85-1792291 (State or other jurisdiction of incorporation)

February 18, 2025 EX-3.1

Class C Certificate of Designations

Exhibit 3.1 Execution Version KINGSWAY FINANCIAL SERVICES INC. CERTIFICATE OF DESIGNATIONS OF CLASS C PREFERRED STOCK Pursuant to Section 151 of the Delaware General Corporation Law (as amended, supplemented or restated from time to time, the “DGCL”), Kingsway Financial Services Inc., a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), in accordance wi

February 18, 2025 EX-10.1

Form of Subscription Agreement - Legal Entity

Exhibit 10.1 Execution Version SUBSCRIPTION AGREEMENT – LEGAL ENTITY This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of February [ ], 2025 by and between , a (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption from securi

February 18, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 12, 2025 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware 001-15204 85-1792291 (State or other jurisdiction of incorporation)

February 18, 2025 EX-10.2

Form of Subscription Agreement - Individual Investor

Exhibit 10.2 Execution Version SUBSCRIPTION AGREEMENT - INDIVIDUAL This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of February [ ], 2025 by and between , a resident of (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption f

February 14, 2025 EX-1.C

SCHEDULE C Transactions in Securities Transactions by Stilwell Activist Fund, L.P.

EX-1.C 4 ex1cto13da4310318011021425.htm SCHEDULE C - TRANSACTIONS IN SECURITIES SCHEDULE C Transactions in Securities Transactions by Stilwell Activist Fund, L.P. Nature of Transaction Date Number of Securities Price Per Share Total Purchase Price Purchase of Class C Preferred Stock 02/12/25 6,400 25.0000 160,000.00 Transactions by Stilwell Activist Investments, L.P. Nature of Transaction Date Num

February 14, 2025 EX-1.B

SCHEDULE B Item 2(e)

EX-1.B 3 ex1bto13da4310318011021425.htm SCHEDULE B - ITEM 2(E) SCHEDULE B Item 2(e) On September 25, 2024, Stilwell Value LLC consented to the entry of a Securities and Exchange Commission (“SEC”) administrative cease and desist order (the “Order”) that, among other things, alleges violations of Section 13(d)(1) and 13(d)(2) of the Securities Exchange Act of 1934 and rules 13d-1 and 13d-2 promulga

February 14, 2025 EX-1.A

SCHEDULE A Stilwell Activist History

EX-1.A 2 ex1ato13da4310318011021425.htm SCHEDULE A - STILWELL ACTIVIST HISTORY SCHEDULE A Stilwell Activist History Since 2000, members or affiliates of the Group have taken an “activist position” in 76 other publicly-traded companies. In each instance, our purpose has been to profit from the appreciation in the market price of the shares we held by asserting shareholder rights. In addition, we be

December 20, 2024 EX-1.C

SCHEDULE C Transactions in Securities Transactions by Stilwell Activist Fund, L.P.

SCHEDULE C Transactions in Securities Transactions by Stilwell Activist Fund, L.P. Nature of Transaction Date Number of Securities Price Per Share Total Sale Price Sale of Common Stock 11/06/24 1,336 9.5500 12,758.80 Sale of Common Stock 11/19/24 2,613 8.7808 22,944.23 Sale of Common Stock 12/18/24 42,416 8.4300 357,566.88 Sale of Common Stock 12/19/24 26,131 8.4300 220,284.33 Transactions by Stil

December 20, 2024 EX-1.A

SCHEDULE A Stilwell Activist History

SCHEDULE A Stilwell Activist History Since 2000, members or affiliates of the Group have taken an "activist position" in 76 other publicly-traded companies.

December 20, 2024 EX-1.B

SCHEDULE B Item 2(e)

SCHEDULE B Item 2(e) On September 25, 2024, Stilwell Value LLC consented to the entry of a Securities and Exchange Commission (“SEC”) administrative cease and desist order (the “Order”) that, among other things, alleges violations of Section 13(d)(1) and 13(d)(2) of the Securities Exchange Act of 1934 and rules 13d-1 and 13d-2 promulgated thereunder for failing to timely file certain beneficial ownership reports on Schedule 13D and Schedule 13G.

November 6, 2024 EX-99.1

KINGSWAY REPORTS Third QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS Third QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago - (November 6, 2024) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and nine months ended September 30, 2024. Third Quarter 2024 Consolidated Financial Highlights ● Consolidated revenue inc

November 6, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

November 6, 2024 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 6, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

September 27, 2024 EX-10.2

Form of Subscription Agreement - Individual Investor

Exhibit 10.2 SUBSCRIPTION AGREEMENT - INDIVIDUAL This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of September 17, 2024 by and between , a resident of (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption from securities reg

September 27, 2024 8-K

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

-12-31 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 24, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation) 001-15204 (Co

September 27, 2024 EX-99.1

KINGSWAY ANNOUNCES $19.5 MILLION ACQUISITION OF IMAGE SOLUTIONS LLC Management to Host Conference Call Wednesday, October 16, at 5 p.m. ET

Exhibit 99.1 KINGSWAY ANNOUNCES $19.5 MILLION ACQUISITION OF IMAGE SOLUTIONS LLC Management to Host Conference Call Wednesday, October 16, at 5 p.m. ET ● Expected to be immediately accretive ● Adds $9.8 million of annual unaudited revenue and $3.1 million of annual unaudited adjusted EBITDA ● Capital light, highly recurring revenue business in stable and growing market ● Latest acquisition under t

September 27, 2024 EX-10.1

Form of Subscription Agreement - Legal Entity

Exhibit 10.1 SUBSCRIPTION AGREEMENT – LEGAL ENTITY This SUBSCRIPTION AGREEMENT (this “Agreement”) is entered into as of September 17, 2024 by and between , a (the “Subscriber”), and Kingsway Financial Services Inc., a Delaware corporation (the “Company”). WHEREAS, the Company and the Subscriber are executing and delivering this Agreement in reliance upon the exemption from securities registration

September 27, 2024 EX-3.1

Certificate of Incorporation of Kingsway Financial Services Inc.

Exhibit 3.1 KINGSWAY FINANCIAL SERVICES INC. CERTIFICATE OF DESIGNATIONS OF CLASS B PREFERRED STOCK Pursuant to Section 151 of the Delaware General Corporation Law (as amended, supplemented or restated from time to time, the “DGCL”), Kingsway Financial Services Inc., a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), in accordance with the provisions

September 27, 2024 EX-10.4

Credit Agreement, dated as of September 26, 2024, between Image Solutions, LLC, Steel Bridge Acquisition LLC and Avidbank*

Exhibit 10.4 CREDIT AGREEMENT dated as of September 26, 2024 IMAGE SOLUTIONS, LLC, a North Carolina limited liability company, as Borrower 1, STEEL BRIDGE ACQUISITION LLC, a Delaware limited liability company, as Borrower 2 and AVIDBANK, a California banking corporation, as Bank $8,250,000 TABLE OF CONTENTS Page ARTICLE I LOAN FACILITIES 3 1.1 Revolving Loans 3 1.2 Term Loan. 3 1.3 Reserved. 4 1.4

September 27, 2024 EX-10.3

Membership Interest Purchase Agreement, dated as of September 26, 2024, by and among Steel Bridge Acquisition LLC, Image Solutions, LLC, Post IS Holdings, LLC and Garrett S. Williams*

Exhibit 10.3 MEMBERSHIP INTEREST PURCHASE AGREEMENT BY AND AMONG STEEL BRIDGE ACQUISITION LLC, AS BUYER, IMAGE SOLUTIONS, LLC, AS THE COMPANY, POST IS HOLDINGS, LLC, AS SELLER, AND GARRETT S. WILLIAMS, AS OWNER, Dated as of September 26, 2024 NO AGREEMENT, ORAL OR WRITTEN, REGARDING OR RELATING TO ANY OF THE MATTERS COVERED BY THIS DRAFT AGREEMENT HAS BEEN ENTERED INTO BETWEEN OR AMONG ANY OF THE

August 6, 2024 EX-99.1

KINGSWAY REPORTS SECOND QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS SECOND QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago - (August 6, 2024) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and six months ended June 30, 2024. Second Quarter 2024 Consolidated Financial Highlights ● Consolidated revenue increased

August 6, 2024 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 6, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

August 6, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

May 29, 2024 EX-10.1

Third Amendment to Loan and Security Agreement, dated May 24, 2024, by and among CIBC Bank USA, Kingsway Warranty Holdings LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation, PWI Holdings, Inc. and the other Loan Parties party thereto

Exhibit 10.1 THIRD AMENDMENT TO LOAN AND SECURITY AGREEMENT This Third Amendment to Loan and Security Agreement (this “Third Amendment”) is made and entered into as of May 24, 2024, by and among CIBC Bank USA, with an office located at 120 South LaSalle Street, Chicago, Illinois 60603 (“Lender”), Kingsway Warranty Holdings LLC, a Delaware limited liability company (“KWH”), Trinity Warranty Solutio

May 29, 2024 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 24, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 21, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 21, 2024 KINGSWAY FINANCIAL S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 21, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 20, 2024 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 20, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 8, 2024 EX-99.1

KINGSWAY REPORTS FIRST QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Management to Host Investor Day on Monday, May 20 in New York City

Exhibit 99.1 KINGSWAY REPORTS FIRST QUARTER 2024 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Management to Host Investor Day on Monday, May 20 in New York City Chicago - (May 8, 2024) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three months ended March 31, 2024. First Quarter 2024 Consolidate

May 8, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

May 8, 2024 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 8, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 1, 2024 EX-99.1

KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS

Exhibit 99.1 KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS Chicago (May 1, 2024) ‐ (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that a letter to its shareholders from John T. Fitzgerald, the Company’s President and CEO, has been made available (the “Letter”). The Letter can be found on the Company’s website at: https://bit.ly/23AL Ab

May 1, 2024 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 1, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 1, 2024 EX-99.2

ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

Exhibit 99.2 ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC. May 1, 2024 Dear Fellow Shareholder, 2023 was a year of significant accomplishments in executing our strategic plan. We delivered financial results largely in-line with our expectations given current market conditions, and we completed two acquisitions of wonderful operating businesses in our KSX segment. We simultaneou

April 10, 2024 DEF 14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

April 10, 2024 DEFA14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

March 22, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 22, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

March 5, 2024 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware Kingsway General Insurance Company Ontario Kingsway Reinsurance Corporation Barbados Kingsway America Inc. Delaware CMC Acquisition LLC Delaware CMC Industries Inc Texas Texas Rail Terminal LLC Delaware TRT Leaseco, LLC Delaware Argo Holdings Fund I,

March 5, 2024 EX-97.1

Incentive Compensation Clawback Policy

Exhibit 97.1 INCENTIVE COMPENSATION CLAWBACK POLICY The Board of Directors (the “Board”) of Kingsway Financial Services Inc. (the “Company”) believes that it is in the best interests of the Company to adopt this Incentive Compensation Clawback Policy (the “Policy”), which provides for the recovery of certain incentive compensation in the event of an Accounting Restatement (as defined below). This

March 5, 2024 EX-99.1

KINGSWAY REPORTS FULL YEAR 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Save the Date: Kingsway to also Host Investor Day at the New York Stock Exchange on May 20, 2024

Exhibit 99.1 KINGSWAY REPORTS FULL YEAR 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Save the Date: Kingsway to also Host Investor Day at the New York Stock Exchange on May 20, 2024 CHICAGO, March 5, 2024 - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the twelve months ended December 31, 2023, a

March 5, 2024 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 5, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

March 5, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

January 16, 2024 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 16, 2024 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

January 12, 2024 SC 13G/A

KFS / Kingsway Financial Services Inc. / David Capital Partners, Llc - AMENDMENT TO FORM SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A (Amendment No. 3)* Under the Securities Exchange Act of 1934 Kingsway Financial Services (Name of Issuer) Common Stock (Titles of Class of Securities) 496904202 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

December 29, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 23, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 21, 2023 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

SC 13D/A 1 tm2331318d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 41) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto R

November 7, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

November 7, 2023 EX-99.1

KINGSWAY REPORTS THIRD QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS THIRD QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago (November 7, 2023) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and nine months ended September 30, 2023. Third Quarter 2023 Consolidated Financial Highlights ● Consolidated revenue incre

November 7, 2023 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 7, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

October 30, 2023 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 26, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

October 30, 2023 EX-10.1

Stock Purchase Agreement by and among Thomas J. Corney and TC Family 2023 LLC, as Sellers, and DDI Acquisition LLC, as Buyer, dated October 26, 2023

Exhibit 10.1 EXECUTION VERSION STOCK PURCHASE AGREEMENT BY AND AMONG THOMAS J. CORNEY AND TC FAMILY 2023 LLC, AS SELLERS, AND DDI ACQUISITION LLC, AS BUYER Dated as of October 26, 2023 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS 1 ARTICLE II PURCHASE AND SALE 9 Section 2.01 Purchase and Sale 9 Section 2.02 Purchase Price 9 Section 2.03 Transactions to be Effected at the Closing. 9 Section 2.04 Ad

October 30, 2023 EX-99.1

KINGSWAY ANNOUNCES $11 MILLION ACQUISITION OF DIGITAL DIAGNOSTICS IMAGING, INC. Management to Host Conference Call Tuesday, October 31, at 5 p.m. ET

Exhibit 99.1 KINGSWAY ANNOUNCES $11 MILLION ACQUISITION OF DIGITAL DIAGNOSTICS IMAGING, INC. Management to Host Conference Call Tuesday, October 31, at 5 p.m. ET ● Expected to be immediately accretive ● Adds $4.2 million of annual unaudited revenue and $1.8 million of annual unaudited adjusted EBITDA ● Capital light, recurring revenue business in stable and growing market ● Latest acquisition unde

October 23, 2023 EX-10.1

Membership Interest Purchase Agreement by and among National Institute of Clinical Research, as Seller, Dr. Sali Aswad, as the Shareholder, and Kingsway Search Xcelerator, Inc., as the Buyer, dated October [19], 2023*.

Exhibit 10.1 MEMBERSHIP INTEREST PURCHASE AGREEMENT BY AND AMONG NATIONAL INSTITUTE OF CLINICAL RESEARCH, AS SELLER, DR. SALI ASWAD, AS THE SHAREHOLDER, AND KINGSWAY SEARCH XCELERATOR INC., AS BUYER Dated as of October 19, 2023 NO AGREEMENT, ORAL OR WRITTEN, REGARDING OR RELATING TO ANY OF THE MATTERS COVERED BY THIS DRAFT AGREEMENT HAS BEEN ENTERED INTO BETWEEN THE PARTIES. THIS DOCUMENT, IN ITS

October 23, 2023 EX-99.1

KINGSWAY SIGNS $7.9 MILLION DEFINITIVE PURCHASE AGREEMENT TO ACQUIRE NATIONAL INSTITUTE OF CLINICAL RESEARCH, INC. Latest acquisition under the Kingsway Search Xcelerator Program

Exhibit 99.1 KINGSWAY SIGNS $7.9 MILLION DEFINITIVE PURCHASE AGREEMENT TO ACQUIRE NATIONAL INSTITUTE OF CLINICAL RESEARCH, INC. Latest acquisition under the Kingsway Search Xcelerator Program Chicago (October 23, 2023) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced the signing of a definitive agreement to purchase 95% of the shares of National Institut

October 23, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 19, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

September 28, 2023 15-12G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number: 001-15204 KINGSWAY FINANCIAL SERVICES INC. (Exact name of registrant as spe

September 11, 2023 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 11, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commissio

September 11, 2023 EX-99.1

KINGSWAY ANNOUNCES FORMATION OF VERTICAL MARKET SOLUTIONS, LLC (“VMS”) AND ACQUISITION OF SYSTEMS PRODUCTS INTERNATIONAL, INC. KINGSWAY SEARCH XCLERATOR ANNOUNCES ADDITION OF MILES MAMON Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY ANNOUNCES FORMATION OF VERTICAL MARKET SOLUTIONS, LLC (“VMS”) AND ACQUISITION OF SYSTEMS PRODUCTS INTERNATIONAL, INC. KINGSWAY SEARCH XCLERATOR ANNOUNCES ADDITION OF MILES MAMON Management to Host Conference Call Today at 5 p.m. ET ● Fourth acquisition under the Kingsway Search Xcelerator Program, first in 2023 ● High margin, capital light, recurring revenue business ● VMS fo

August 8, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

August 8, 2023 EX-99.1

KINGSWAY REPORTS SECOND QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS SECOND QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago (August 8, 2023) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and six months ended June 30, 2023. Second Quarter 2023 Consolidated Financial Highlights ● Consolidated revenue increased 1

August 8, 2023 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 8, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

May 18, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 16, 2023 KINGSWAY FINANCIAL S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 16, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 11, 2023 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 40) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

May 9, 2023 EX-99.1

KINGSWAY REPORTS FIRST QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Management to Host Investor Day on Tuesday, May 16 in New York City

Exhibit 99.1 KINGSWAY REPORTS FIRST QUARTER 2023 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Management to Host Investor Day on Tuesday, May 16 in New York City Chicago – May 9, 2023 – (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its financial results for the three months ended March 31, 2023. First Quarter 2023 Consolidated

May 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

May 9, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 9, 2023 KINGSWAY FINANCIAL SE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 9, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

April 21, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 21, 2023 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 21, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

April 17, 2023 EX-99.1

KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS

Exhibit 99.1 KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS Chicago (April 17, 2023) ‐ (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that a letter to its shareholders from John T. Fitzgerald, the Company’s President and CEO, has been made available (the “Letter”). The Letter can be found on the Company’s website at: http://bit.ly/kfs20

April 17, 2023 EX-99.2

ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

Exhibit 99.2 ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC. April 17, 2023 Dear Fellow Shareholder, The year 2022 was an excellent one for Kingsway Financial Services Inc., with significant achievements in executing our strategic plan. We are proud to have delivered strong financial results while simultaneously streamlining our capital structure through the sale of non-strategic

April 17, 2023 EX-99.3

Page | 2

Exhibit 99.3 A view from Kingsway’s newest director. I joined the Kingsway Board in May of 2022 and I wanted to write this addendum to the CEO’s letter to shareholders to provide some insights into the company and my experience to date. I have been investing in public companies for the past 35 years and have learned that the goals of management and shareholders are often far apart. Management in m

April 17, 2023 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 17, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

April 6, 2023 DEFA14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

April 6, 2023 DEF 14A

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. )

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: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

March 21, 2023 EX-99.1

Kingsway Financial Services Inc. Board of Directors Authorizes Share Repurchase Plan

Exhibit 99.1 Kingsway Financial Services Inc. Board of Directors Authorizes Share Repurchase Plan Chicago (March 21, 2023) – (NYSE: KFS) – Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that its Board of Directors approved a share repurchase program that authorizes the Company to repurchase up to $10 million of its common stock. The share repurchase program will hav

March 21, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 21, 2023 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 21, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

March 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 20, 2023 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 20, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

March 20, 2023 EX-99.1

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

Exhibit 99.1 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 Once all repurchases are completed, pro forma subordinated debt as of December 31, 2022 would be $11.4 million and pro forma deferred interest payable would be zero CHICAGO (March 20, 2023) - (NYSE: KFS)

March 14, 2023 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 39) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

March 8, 2023 EX-99.1

KINGSWAY REPORTS FULL YEAR 2022 RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS FULL YEAR 2022 RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago (March 8, 2023) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the 12 months ended December 31, 2022. Recent Business Highlights ● Completed the sale of its railyard in Texas for $215.2 million, consisting of $44.

March 8, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

March 8, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 8, 2023 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 8, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

March 8, 2023 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware 1347 Advisors LLC Delaware Argo Holdings Fund I, LLC Delaware Argo Management Group, LLC Delaware CMC Acquisition LLC Delaware CMC Industries Inc Texas Texas Rail Terminal LLC Delaware TRT Leaseco, LLC Delaware Flower Portfolio 001, LLC Delaware King

March 8, 2023 EX-10.24

Second Amendment to Loan and Security Agreement, dated as of February 28, 2023, among Kingsway Warranty Holdings LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation and PWI Holdings, Inc., as Borrowers, the other Loan Parties party thereto, and CIBC Bank USA, as Lender and as Issuing Lender.

Exhibit 10.24 SECOND AMENDMENT TO LOAN AND SECURITY AGREEMENT This Second Amendment to Loan and Security Agreement (this “Second Amendment”) is made and entered into as of February 28, 2023, by and among CIBC Bank USA, with an office located at 120 South LaSalle Street, Chicago, Illinois 60603 (“Lender”), Kingsway Warranty Holdings LLC, a Delaware limited liability company (“KWH”), Trinity Warrant

March 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 2, 2023 KINGSWAY FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 2, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation) (Com

March 1, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 28, 2023 KINGSWAY FINANC

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 28, 2023 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation)

January 12, 2023 SC 13G/A

KFS / Kingsway Financial Services Inc / David Capital Partners, Llc - AMENDMENT TO FORM SC 13G Passive Investment

SC 13G/A 1 kfs-sc13ga123122.htm AMENDMENT TO FORM SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A (Amendment No. 2)* Under the Securities Exchange Act of 1934 Kingsway Financial Services (Name of Issuer) Common Stock (Titles of Class of Securities) 496904202 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check

January 5, 2023 EX-99.2

Kingsway Financial Services Inc. Unaudited Pro Forma Consolidated Financial Statements

Exhibit 99.2 Kingsway Financial Services Inc. Unaudited Pro Forma Consolidated Financial Statements On December 22, 2022, Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) entered into an agreement for the sale of certain assets and the assumption of certain liabilities of TRT LeaseCo, a subsidiary of CMC Industries, Inc. (?CMC?) to BNSF Dayton LLC for cash and certain additional cons

January 5, 2023 EX-99.1

Kingsway Completes Sale of Texas Railyard for $21.4 Million of Net Cash Proceeds to The Company

Exhibit 99.1 Kingsway Completes Sale of Texas Railyard for $21.4 Million of Net Cash Proceeds to The Company CHICAGO, Dec. 29, 2022 /CNW/ - (NYSE: KFS) Kingsway Financial Services Inc. ("Kingsway" or the "Company") today announced it has closed on the sale of the railyard it owns in Texas. TRT Leaseco, LLC, an indirect subsidiary of the Company and direct owner of the railyard, completed the sale

January 5, 2023 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 29, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

January 4, 2023 SC 13D/A

KFS / Kingsway Financial Services Inc / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 38) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

December 23, 2022 EX-10.1

Purchase and Sale Agreement dated December 22, 2022, by and between TRT Leaseco, LLC, as Seller, and BNSF Dayton LLC, as Purchaser

EX-10.1 2 ea170787ex10-1kingsway.htm PURCHASE AND SALE AGREEMENT DATED DECEMBER 22, 2022, BY AND BETWEEN TRT LEASECO, LLC, AS SELLER, AND BNSF DAYTON LLC, AS PURCHASER Exhibit 10.1 PURCHASE AND SALE AGREEMENT THIS PURCHASE AND SALE AGREEMENT (this “Agreement”) is entered into as of the Effective Date (hereinafter defined) by and between TRT LEASECO, LLC, a Delaware limited liability company (“Sell

December 23, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 22, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation)

November 21, 2022 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 18, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 21, 2022 EX-99.1

KINGSWAY ANNOUNCES ACQUISITION OF SECURE NURSING SERVICE, INC.

Exhibit 99.1 KINGSWAY ANNOUNCES ACQUISITION OF SECURE NURSING SERVICE, INC. ? Third acquisition under the Kingsway Search Xcelerator Program ? Expected to be immediately accretive, adding $19.7 million of unaudited revenue, $2.6 million of U.S. GAAP income before income taxes and $2.7 million of unaudited non-GAAP adjusted EBITDA ? Capital light, recurring revenue business Chicago (November 21, 20

November 21, 2022 EX-10.1

Asset purchase agreement by and among Pegasus acquirer LLC, as buyer, Secure Nursing Service, Inc., as seller and Rafael Gofman, Ella Gofman And Zhanna Weiss, as the shareholders

EX-10.1 2 ex449258.htm EXHIBIT 10.1 Exhibit 10.1 EXECUTION VERSION ASSET PURCHASE AGREEMENT BY AND AMONG PEGASUS ACQUIRER LLC, AS BUYER, SECURE NURSING SERVICE, INC., AS SELLER AND RAFAEL GOFMAN, ELLA GOFMAN AND ZHANNA WEISS, AS THE SHAREHOLDERS Dated as of November 18, 2022 TABLE OF CONTENTS Page ARTICLE I CERTAIN DEFINITIONS 1 ARTICLE II PURCHASE AND SALE 12 Section 2.01 Purchase and Sale 12 Sec

November 10, 2022 EX-99.1

KINGSWAY REPORTS THIRD QUARTER 2022 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET

Exhibit 99.1 KINGSWAY REPORTS THIRD QUARTER 2022 FINANCIAL RESULTS Management to Host Conference Call Today at 5 p.m. ET Chicago (November 10, 2022) - (NYSE: KFS) Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) today announced its operating results for the three and nine months ended September 30, 2022. Recent Business Highlights ? Completed the sale of its Professional Warranty Ser

November 10, 2022 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 10, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 10, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

November 2, 2022 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2022 KINGSWAY FINANCI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 2, 2022 EX-99.1

KINGSWAY ANNOUNCES ACQUISITION OF CSUITE FINANCIAL PARTNERS

Exhibit 99.1 KINGSWAY ANNOUNCES ACQUISITION OF CSUITE FINANCIAL PARTNERS ● Expected to be immediately accretive, adds $9.4 million of unaudited revenue, $0.9 million U.S. GAAP income before income taxes and $1.8 million of unaudited non-GAAP adjusted EBITDA ● Second acquisition under the Kingsway Search Xcelerator Program ● Capital light, re-occurring revenue business ● Will be run alongside Ravix

November 2, 2022 EX-10.1

Membership Interest Purchase Agreement by and among CSuite Acquisition, LLC, Arthur J. Cohen and Beth Garden, as Trustees of the Cohen Garden Trust dated July 13, 2015, Realized Potential, LLC, and Arthur J. Cohen, as the Sellers’ Representative, dated November 1, 2022

Exhibit 10.1 EXECUTION VERSION MEMBERSHIP INTEREST PURCHASE AGREEMENT BY AND AMONG CSUITE ACQUISITION LLC, AS BUYER, ARTHUR J. COHEN, AS THE SELLERS’ REPRESENTATIVE, AND THE SELLERS IDENTIFIED HEREIN Dated as of November 1, 2022 TABLE OF CONTENTS Page ARTICLE I CERTAIN DEFINITIONS 1 ARTICLE II PURCHASE AND SALE 10 Section 2.01 Purchase and Sale 10 Section 2.02 Purchase Price 10 Section 2.03 Transa

August 4, 2022 EX-99.2

Kingsway Financial Services Inc. Unaudited Pro Forma Consolidated Financial Statements

Exhibit 99.2 Kingsway Financial Services Inc. Unaudited Pro Forma Consolidated Financial Statements On July 29, 2022, Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) completed the sale of Professional Warranty Services Corporation (?PWSC?) to PCF Insurance Services of the West, LLC for cash and certain additional consideration. PWSC had been included in the Extended Warranty segment

August 4, 2022 EX-2.1

Stock Purchase Agreement, dated July 29, 2022, by and among Professional Warranty Service Corporation, a Virginia corporation (the “Company”) Tyler Gordy, an individual (“Gordy”); Professional Warranty Services LLC, a Delaware limited liability company (“Parent” and together with Gordy, each a “Seller” and collectively “Sellers”); and PCF Insurance Services of the West, LLC, a Delaware limited liability company (“Buyer”)

EX-2.1 2 ex405061.htm EXHIBIT 2.1 Exhibit 2.1 EQUITY PURCHASE AGREEMENT This EQUITY PURCHASE AGREEMENT (this “Agreement”) is dated as of July 29, 2022 (the “Effective Date”), and is by and among Professional Warranty Service Corporation, a Virginia corporation (the “Company”) Tyler Gordy, an individual (“Gordy”); Professional Warranty Services LLC, a Delaware limited liability company (“Parent” an

August 4, 2022 8-K

Regulation FD Disclosure, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 29, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

August 4, 2022 EX-99.1

KINGSWAY REPORTS SECOND QUARTER 2022 RESULTS AND ANNOUNCES SALE OF PWSC FOR $51.2 MILLION, ENTRANCE INTO AN OPTION AGREEMENT TO REPURCHASE A PORTION OF ITS DEBT

Exhibit 99.1 KINGSWAY REPORTS SECOND QUARTER 2022 RESULTS AND ANNOUNCES SALE OF PWSC FOR $51.2 MILLION, ENTRANCE INTO AN OPTION AGREEMENT TO REPURCHASE A PORTION OF ITS DEBT Itasca, Illinois (August 4, 2022) - (NYSE: KFS) Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) today announced its operating results for the three and six months ended June 30, 2022; the sale of PWSC for $51.2

August 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

July 18, 2022 SC 13D/A

KFS / Kingsway Financial Services Inc / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 37) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

June 22, 2022 SC 13D/A

KFS / Kingsway Financial Services Inc / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 36) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

May 20, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 17, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 20, 2022 EX-99.1

KINGSWAY ANNOUNCES EXPANSION OF BOARD – APPOINTMENT OF NEW DIRECTOR

EX-99.1 2 ex378493.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY ANNOUNCES EXPANSION OF BOARD – APPOINTMENT OF NEW DIRECTOR Itasca, Illinois (May 20, 2022) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that Charles Frischer was appointed to its Board of Directors. Mr. Frischer was also appointed to serve on the Audit Committee and the newly created Real Esta

May 20, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 17, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 6, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

May 6, 2022 EX-99.1

KINGSWAY REPORTS FIRST QUARTER 2022 RESULTS

Exhibit 99.1 KINGSWAY REPORTS FIRST QUARTER 2022 RESULTS Itasca, Illinois (May 6, 2022) - (NYSE: KFS) Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) today announced its operating results for the three months ended March 31, 2022. John T. Fitzgerald, President and Chief Executive Officer, stated, ?We had a good start to the year with results largely exceeding our initial expectation

May 6, 2022 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

April 7, 2022 DEF 14A

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. )

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: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

April 7, 2022 DEFA14A

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. )

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: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

March 28, 2022 SC 13D/A

KFS / Kingsway Financial Services Inc / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 35) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

February 28, 2022 8-K

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 28, 2022 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

February 28, 2022 EX-99.2

ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

Exhibit 99.2 ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC. February 28, 2022 Dear Fellow Shareholder, I am pleased to be sharing this letter with you in connection with the issuance of our 2021 Annual Report. I?m proud of the considerable forward progress we made as a company in the past year. Some of the highlights include: ? Revenues in our extended warranty segment grew by 5

February 28, 2022 EX-99.1

KINGSWAY REPORTS FULL YEAR 2021 RESULTS – PUBLISHES ANNUAL SHAREHOLDER LETTER

Exhibit 99.1 KINGSWAY REPORTS FULL YEAR 2021 RESULTS – PUBLISHES ANNUAL SHAREHOLDER LETTER Itasca, Illinois (February 28, 2022) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the twelve months ended December 31, 2021, which includes the following highlights: ● Net income improved to $1.9 million for the twelve months ended Dec

February 28, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

February 28, 2022 EX-21

Subsidiaries of Kingsway Financial Services Inc.

EX-21 2 ex289865.htm EXHIBIT 21 Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware 1347 Advisors LLC Delaware Argo Holdings Fund I, LLC Delaware Argo Management Group, LLC Delaware CMC Acquisition LLC Delaware CMC Industries Inc. Texas Texas Rail Terminal LLC Delaware TRT Leaseco, LLC Delaware Flower

January 12, 2022 SC 13G/A

KFS / Kingsway Financial Services Inc / David Capital Partners, Llc - AMENDMENT TO FORM SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A (Amendment No. 1)* Under the Securities Exchange Act of 1934 Kingsway Financial Services (Name of Issuer) Common Stock (Titles of Class of Securities) 496904202 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

November 29, 2021 SC 13D/A

KFS / Kingsway Financial Services Inc / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 34) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 200 Calle del Santo Cristo Segundo Piso San Juan, Puerto Ric

November 5, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2021 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

November 5, 2021 EX-4.7

SECOND AMENDED AND RESTATED KINGSWAY FINANCIAL SERVICES INC. COMMON STOCK SERIES B WARRANT AGREEMENT

EXHIBIT 4.7 SECOND AMENDED AND RESTATED KINGSWAY FINANCIAL SERVICES INC. COMMON STOCK SERIES B WARRANT AGREEMENT This Second Amended and Restated Common Stock Warrant Agreement (this ?Agreement?), dated as of , 2021, between Kingsway Financial Services Inc., a Delaware corporation (the ?Company?), Computershare Inc., a Delaware corporation (?Co-Agent?), and its wholly owned subsidiary, Computersha

November 4, 2021 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 4, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 4, 2021 EX-99.1

KINGSWAY REPORTS THIRD QUARTER 2021 RESULTS

EX-99.1 2 ex280567.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY REPORTS THIRD QUARTER 2021 RESULTS Itasca, Illinois (November 4, 2021) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and nine months ended September 30, 2021, which includes the following highlights: ● Net loss improved to ($0.2) million for the three months

October 6, 2021 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 6, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation) (C

October 4, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 1, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation) (C

October 4, 2021 EX-10.1

Stock Purchase Agreement by and among, Ravix Acquisition, LLC, The Shareholders of Ravix Financial, Inc., Ravix Financial, Inc., Kingsway America, Inc.

Exhibit 10.1 Execution Copy STOCK PURCHASE AGREEMENT by and among, RAVIX ACQUISITION, LLC, THE SHAREHOLDERS OF RAVIX FINANCIAL, INC., RAVIX FINANCIAL, INC., KINGSWAY AMERICA, INC. (solely with respect to Section 9.21), and Dan Saccani, as the Seller Representative Dated October 1, 2021 TABLE OF CONTENTS Page STOCK PURCHASE AGREEMENT 1 ARTICLE 1 PURCHASE AND SALE OF COMPANY SECURITIES 1 1.1 Transac

October 4, 2021 EX-99.1

KINGSWAY EXPANDS INTO ACCOUNTING & HR OUTSOURCING

Exhibit 99.1 KINGSWAY EXPANDS INTO ACCOUNTING & HR OUTSOURCING Itasca, Illinois (October 4, 2021) ? (NYSE: KFS) Kingsway Financial Services Inc. (?Kingsway?) today announced the acquisition of the privately-held company Ravix Financial Inc. (?Ravix?), the first such acquisition completed under Kingsway?s unique CEO Accelerator Program. Ravix, based in San Jose, California (www.ravixgroup.com) prov

August 5, 2021 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 5, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

August 5, 2021 EX-99.1

KINGSWAY REPORTS SECOND QUARTER 2021 RESULTS

Exhibit 99.1 KINGSWAY REPORTS SECOND QUARTER 2021 RESULTS Itasca, Illinois (August 5, 2021) - (NYSE: KFS) Kingsway Financial Services Inc. (?Kingsway? or the ?Company?) today announced its operating results for the three and six months ended June 30, 2021, which includes the following highlights: ? Net loss improved to ($0.3) million for the three months ended June 30, 2021, from a net loss of ($1

August 5, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

June 15, 2021 SC 13D/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 33) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securit

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 33) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 111 Broadway, 12th Floor New York, New York 10006 Telephone:

June 4, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 28, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 17, 2021 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 17, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 13, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2021 or o TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2021 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

May 12, 2021 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 12, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

May 12, 2021 EX-99.1

Kingsway Financial Services Inc. Consolidated Balance Sheets (in thousands, except share data)

EX-99.1 2 a2021q1earningsrelease0511.htm EX-99.1 Exhibit 99.1 KINGSWAY REPORTS FIRST QUARTER 2021 RESULTS Itasca, Illinois (May 12, 2021) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three months ended March 31, 2021, which includes the following highlights: •Net income was $0.9 million for the three months ended March 3

May 3, 2021 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 3, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

April 27, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 2, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 31, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-15204 85-1792291 (State or Other Jurisdiction of Incorporation) (Co

April 2, 2021 SC 13D

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. __)*

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No.

April 2, 2021 EX-10.1

Employment Separation Agreement and Release, by and between Kingsway America, Inc. and Paul R. Hogan, dated as of March 31, 2021.

EX-10.1 2 ea138906ex10-1kingsway.htm EMPLOYMENT SEPARATION AGREEMENT AND RELEASE, BY AND BETWEEN KINGSWAY AMERICA, INC. AND PAUL R. HOGAN, DATED AS OF MARCH 31, 2021 Exhibit 10.1 EMPLOYMENT SEPARATION AGREEMENT AND RELEASE This EMPLOYMENT SEPARATION AGREEMENT AND RELEASE (“Agreement”) is made and entered into by and between Kingsway America Inc., a Delaware corporation (“Employer”), and Paul R. Ho

March 29, 2021 EX-99.2

KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS

EX-99.2 3 exhibit992-pressreleasexma.htm EX-99.2 Exhibit 99.2 KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS Itasca, Illinois (March 29, 2021) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that a letter to its shareholders from John T. Fitzgerald, the Company’s President and CEO, has been made available (the “Letter”). The Letter can

March 29, 2021 EX-10.29

Form of Restricted Stock Agreement.

EX-10.29 3 kingsway-formofrestricteds.htm EX-10.29 Exhibit 10.29 KINGSWAY FINANCIAL SERVICES INC. 2020 EQUITY INCENTIVE PLAN Restricted Stock Agreement This Restricted Stock Agreement (“Restricted Stock Agreement”) evidences the grant to [INSERT PARTICIPANT NAME] (the “Participant”) by Kingsway Financial Services Inc. (the “Company”) of the right to receive shares of Common Stock of the Company on

March 29, 2021 EX-10.28

Letter Agreement, effective as of December 31, 2020, by and among Kingsway Warranty Holdings LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation, and PWI Holdings, Inc., as Borrowers, the other Loan Parties party thereto, and CIBC Bank USA, as Lender.

EX-10.28 2 cibckingswaywarrantyconsen.htm EX-10.28 Exhibit 10.28 Dated as of January 11, 2021, but effective as of December 31, 2020 Kingsway Warranty Holdings LLC and Subsidiaries c/o Kingsway Financial Services Inc. 150 Pierce Road, Suite 600 Itasca, Illinois 60143 Attention: Kent A. Hansen Re: Consent Letter Agreement (this “Letter Agreement”) To Whom It May Concern: Reference is hereby made to

March 29, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

March 29, 2021 EX-99.1

Kingsway Financial Services Inc. Consolidated Balance Sheets (in thousands, except share data) December 31, 2020 December 31, 2019 Assets Investments: Fixed maturities, at fair value (amortized cost of $20,488 and $22,136, respectively) $ 20,716 $ 22

Exhibit 99.1 KINGSWAY REPORTS FOURTH QUARTER AND FULL YEAR 2020 RESULTS Itasca, Illinois (March 26, 2021) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and twelve months ended December 31, 2020, which includes the following highlights: •Extended Warranty operating income increased 35% for the twelve months ended Dec

March 29, 2021 EX-99.3

APPENDIX I TO ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

EX-99.3 4 exhibit993-2020kfsannualsh.htm EX-99.3 Exhibit 99.3 Annual Letter to Shareholders of Kingsway Financial Services Inc. March 29, 2021 Dear Fellow Shareholder, I am pleased to be sharing this letter with you in connection with the issuance of our 2020 Annual Report. I’m proud of the meaningful progress we made as a company in the past year in spite of the challenges and uncertainty we enco

March 29, 2021 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware 1347 Advisors LLC Delaware Argo Holdings Fund I, LLC Delaware Argo Management Group, LLC Delaware CMC Acquisition LLC Delaware CMC Industries Inc. Texas Texas Rail Terminal LLC Delaware TRT Leaseco, LLC Delaware Flower Portfolio 001, LLC Delaware Kin

March 29, 2021 8-K

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 26, 2021 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

December 2, 2020 EX-99.1

KINGSWAY CLOSES ACQUISITION OF PWI HOLDINGS

Exhibit 99.1 KINGSWAY CLOSES ACQUISITION OF PWI HOLDINGS Itasca, Illinois (December 1, 2020) – (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway”) today announced the closing of its acquisition of PWI Holdings, Inc. (collectively with its subsidiaries Preferred Warranties, Inc., Superior Warranties, Inc., Preferred Warranties of Florida, Inc., and Preferred Nationwide Reinsurance Company, Lt

December 2, 2020 8-K

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Completion of Acquisition or Disposition of Assets - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 1, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

December 2, 2020 EX-10.1

Loan and Security Agreement, dated as of December 1, 2020, among Kingsway Warranty Holdings LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation and PWI Holdings, Inc., as Borrowers, the other Loan Parties party thereto, and CIBC Bank USA, as Lender and as Issuing Lender

EX-10.1 2 ex101-loanandsecuritya.htm EX-10.1 Exhibit 10.1 1Execution Version LOAN AND SECURITY AGREEMENT dated as of December 1, 2020 between Kingsway Warranty Holdings LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation and PWI Holdings, Inc. as Borrowers, THE OTHER LOAN PARTIES PARTY HERETO and CIBC BANK USA, as Lender 1 Exhibit 10.1 SECTION 1 DEFINITI

November 6, 2020 8-K

Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 6, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

November 6, 2020 EX-99.1

Kingsway Financial Services Inc. Consolidated Balance Sheets (in thousands, except share data) September 30, 2020 December 31, 2019 (unaudited) Assets Investments: Fixed maturities, at fair value (amortized cost of $19,971 and $22,136, respectively)

EX-99.1 2 exhibit99110qq32020results.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY REPORTS THIRD QUARTER 2020 RESULTS Itasca, Illinois (November 6, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced its operating results for the three and nine months ended September 30, 2020, which includes the following highlights: • Net cash provided by operating activiti

November 6, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

October 13, 2020 8-K

Current Report

8-K 1 a8-k101320.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 12, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporatio

October 13, 2020 EX-99.1

KINGSWAY TO EXPAND PORTFOLIO OF WARRANTY HOLDINGS

Exhibit 99.1 KINGSWAY TO EXPAND PORTFOLIO OF WARRANTY HOLDINGS Itasca, Illinois (October 13, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway”) today announced the signing of a definitive agreement to acquire PWI Holdings, Inc. from ADESA Dealer Services, LLC, a subsidiary of (NYSE: KAR) KAR Auction Services, Inc. d/b/a KAR Global (“KAR”), subject to certain regulatory approvals and

October 13, 2020 EX-2.1

Stock Purchase Agreement, dated as of October 12, 2020, by and among Kingsway Warranty Holdings LLC,Kingsway America Inc., PWI Holdings, Inc., and ADESA Dealer Services, LLC

EX-2.1 2 exhibit21projectcolt-stock.htm EXHIBIT 2.1 Exhibit 2.1 [**] INDICATES THAT INFORMATION HAS BEEN REDACTED. Execution Version STOCK PURCHASE AGREEMENT DATED AS OF OCTOBER 12, 2020 BY AND AMONG KINGSWAY WARRANTY HOLDINGS LLC (“BUYER”), PWI HOLDINGS, INC. (THE “COMPANY”), ADESA DEALER SERVICES, LLC (“SELLER”), AND KINGSWAY AMERICA INC. (“PARENT”) 1 Exhibit 2.1 TABLE OF CONTENTS Page ARTICLE I

October 2, 2020 S-8

- S-8

As filed with the Securities and Exchange Commission on October 2, 2020 Registration No.

October 2, 2020 EX-10.1

KINGSWAY FINANCIAL SERVICES INC. 2020 EQUITY INCENTIVE PLAN

EX-10.1 3 exhibit1012020equityincen.htm EXHIBIT 10.1 Exhibit 10.1 KINGSWAY FINANCIAL SERVICES INC. 2020 EQUITY INCENTIVE PLAN 1.Establishment, Purpose and Duration. Kingsway Financial Services Inc. (hereinafter referred to as the “Company”) hereby establishes a long-term incentive compensation plan to be known as the 2020 Equity Incentive Plan (hereinafter referred to as the “Plan”), as set forth

September 22, 2020 8-K

- 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 21, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commissio

September 21, 2020 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 32) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 111 Broadway, 12th Floor New York, New York 10006 Telephone:

September 10, 2020 SC 13G/A

LMB / Limbach Holdings, Inc. / KINGSWAY FINANCIAL SERVICES INC - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (AMENDMENT NO. 1) Limbach Holdings, Inc. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 53263P105 (CUSIP Number) Check the appropriate box to designate the rule pursuant to which this Schedule is filed: ¨ Rule 13d-1(b) x Rule 13d-

September 9, 2020 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 31) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 111 Broadway, 12th Floor New York, New York 10006 Telephone:

August 20, 2020 DEF 14A

Kingsway Financial Services Inc. 2020 Equity Incentive Plan

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

August 13, 2020 EX-99.1

KINGSWAY REPORTS SECOND QUARTER 2020 RESULTS

Exhibit 99.1 KINGSWAY REPORTS SECOND QUARTER 2020 RESULTS Itasca, Illinois (August 13, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today filed its quarterly report on Form 10-Q for the three and six months ended June 30, 2020, which includes the following highlights: • For the three months ended June 30, 2020, operating income was essentially breakeven, compa

August 13, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 13, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission F

August 13, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

August 3, 2020 SC 13D/A

KFS / Kingsway Financial Services Inc. / Frischer Charles Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D under the Securities Exchange Act of 1934 (Amendment No. 2) KINGSWAY FINANCIAL SERVICES INC. (Name of Issuer) Common Stock, $0.01 par value per share (Title of Class of Securities) 496904202 (CUSIP Number of Class of Securities) Charles L. Frischer 4404 52nd Avenue NE Seattle, WA 98105 (Name, Address and Telephone Number of Per

July 22, 2020 EX-99.2

ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

Exhibit 99.2 ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC. July 22, 2020 Dear Fellow Shareholder, I am pleased to be sharing this letter with you in connection with the issuance of our 2019 Annual Report. We made significant progress in 2019 towards our stated objectives of a) focusing on strategic capital allocation; b) executing operational improvements; and c) building a wor

July 22, 2020 EX-99.1

KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS

Exhibit 99.1 KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS Itasca, Illinois (July 22, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that a letter to its shareholders from John T. Fitzgerald, the Company’s President and CEO, has been made available (the “Letter”). The Letter can be found on the Company’s website by following ei

July 22, 2020 EX-99.1

KINGSWAY ANNOUNCES RECEIPT OF NYSE LATE FILER CURE LETTER

EX-99.1 2 exhibit991nyselatefilercure.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY ANNOUNCES RECEIPT OF NYSE LATE FILER CURE LETTER Itasca, Illinois (July 22, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that on July 20, 2020 the Company received a notice letter from the New York Stock Exchange (“NYSE”) stating that, effective July 21, 2020, the Comp

July 22, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 20, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

July 22, 2020 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 22, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

July 17, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

July 17, 2020 SC 13D/A

KFS / Kingsway Financial Services Inc. / STILWELL JOSEPH - SC 13D/A Activist Investment

CUSIP No. 496904202 SCHEDULE 13D Page 1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 30) KINGSWAY FINANCIAL SERVICES Inc. (Name of Issuer) Common Shares, no par value (Title of Class of Securities) 496904202 (CUSIP Number) Mr. Joseph Stilwell 111 Broadway, 12th Floor New York, New York 10006 Telephone:

July 16, 2020 EX-99.1

KINGSWAY ANNOUNCES NYSE ACCEPTANCE OF CONTINUED LISTING COMPLIANCE PLAN

EX-99.1 2 exhibits991-kingswayannoun.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY ANNOUNCES NYSE ACCEPTANCE OF CONTINUED LISTING COMPLIANCE PLAN Itasca, Illinois (July 16, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that the New York Stock Exchange (“NYSE”) has accepted the Company’s business plan to regain compliance with NYSE continued listing sta

July 16, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 9, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission File

July 10, 2020 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

July 10, 2020 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware 1347 Advisors LLC Delaware Argo Holdings Fund I, LLC Delaware Argo Management Group, LLC Delaware CMC Acquisition LLC Delaware CMC Industries Inc. Texas Texas Rail Terminal LLC Delaware TRT Leaseco, LLC Delaware Flower Portfolio 001, LLC Delaware Gem

May 15, 2020 NT 10-Q

- NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K x Form 10-Q ☐ Form 10-D ☐ Form N-SAR ☐ Form N-CSR For Period Ended: March 31, 2020 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transition Report on Form 10-Q ☐ Transition Report on Fo

May 15, 2020 SC 13D/A

KFS / Kingsway Financial Services Inc. / Frischer Charles Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D under the Securities Exchange Act of 1934 (Amendment No. 1) KINGSWAY FINANCIAL SERVICES INC. (Name of Issuer) Common Stock, $0.01 par value per share (Title of Class of Securities) 496904202 (CUSIP Number of Class of Securities) Charles L. Frischer 4404 52nd Avenue NE Seattle, WA 98105 (Name, Address and Telephone Number of Per

April 28, 2020 SC 13D

KFS / Kingsway Financial Services Inc. / Frischer Charles Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D under the Securities Exchange Act of 1934 KINGSWAY FINANCIAL SERVICES INC. (Name of Issuer) Common Stock, $0.01 par value per share (Title of Class of Securities) 496904202 (CUSIP Number of Class of Securities) Charles L. Frischer 4404 52nd Avenue NE Seattle, WA 98105 (Name, Address and Telephone Number of Person Authorized to

April 21, 2020 EX-99.1

KINGSWAY ANNOUNCES RECEIPT OF NOTIFICATION LETTERS FROM NYSE

EX-99.1 2 exhibit991kingswayannounce.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY ANNOUNCES RECEIPT OF NOTIFICATION LETTERS FROM NYSE Itasca, Illinois (April 21, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced it received notice from the New York Stock Exchange (“NYSE”) that the Company is not in compliance with NYSE listing standard 802.01E because it

April 21, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 15, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

April 10, 2020 10-Q

KFS / Kingsway Financial Services Inc. 10-Q - Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Finan

April 10, 2020 10-Q

KFS / Kingsway Financial Services Inc. 10-Q - Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway

April 9, 2020 10-Q

KFS / Kingsway Financial Services Inc. 10-Q - Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fina

March 30, 2020 NT 10-K

KFS / Kingsway Financial Services Inc. NT 10-K - - NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING Check one): x Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-SAR ☐ Form N-CSR For Period Ended: December 31, 2019 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transition Report on Form 10-Q ☐ Transition Report on

March 17, 2020 EX-99.1

KINGSWAY ANNOUNCES RECEIPT OF FURTHER EXTENSION FROM NYSE

Exhibit 99.1 KINGSWAY ANNOUNCES RECEIPT OF FURTHER EXTENSION FROM NYSE Itasca, Illinois (March 16, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that the New York Stock Exchange (“NYSE”) granted the Company an additional extension through April 17, 2020 to become current with all of its periodic Securities and Exchange Commission (“SEC”) filings

March 17, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 13, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fi

March 12, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 6, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

March 12, 2020 EX-99.1

1

EX-99.1 2 exhibit991kingswayllcconso.htm EXHIBIT 99.1 Exhibit 99.1 PURPOSE: To document the considerations made in determining the accounting for Kingsway America Inc.’s and subsidiaries (the “Company”) investments in the following limited liability companies (“LLC’s”). Net Lease Investment Grade Portfolio, LLC (“NLIGP”) Flowers Portfolio 001, LLC (“Flowers”) DPM SPV, LLC (“DPM”) 1347 Venture Oppo

March 12, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 6, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

March 12, 2020 EX-99.2

As Reported as of and

Exhibit 99.2 PURPOSE To document the considerations made in determining the accounting for Kingsway Financial Services Inc.’s (the “Company”) issuance of convertible preferred stock and warrants on February 3, 2014. BACKGROUND On December 20, 2013, the Company entered into subscription agreements to issue and sell in a private placement (the “Private Placement”) to accredited investors an aggregat

March 12, 2020 SC 13G

KFS / Kingsway Financial Services Inc. / David Capital Partners, Llc - ACQUISITION OF BENEFICIAL OWNERSHIP Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Amendment No. )* Under the Securities Exchange Act of 1934 Kingsway Financial Services (Name of Issuer) Common Stock (Titles of Class of Securities) 496904202 (CUSIP Number) March 3, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this

March 12, 2020 EX-16.1

March 12, 2020

Exhibit 16.1 March 12, 2020 Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Commissioners: We have read Kingsway Financial Services Inc.’s statements included in Item 4.01(a) of its Form 8-K filed on March 12, 2020 and we agree with such statements concerning our firm. Sincerely,

March 2, 2020 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 2, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission Fil

March 2, 2020 EX-99.2

ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC.

Exhibit 99.2 KINGSWAY FINANCIAL SERVICES INC. ANNUAL LETTER TO SHAREHOLDERS OF KINGSWAY FINANCIAL SERVICES INC. March 2, 2020 Dear Fellow Shareholder, This is my first letter to you as the CEO of Kingsway Financial Services Inc. (“Kingsway” or “Company). It is long overdue. I am happy to have our 2018 audit behind us, and I look forward to communicating updates on 2019 performance in the weeks to

March 2, 2020 EX-99.1

KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS

Exhibit 99.1 KINGSWAY ANNOUNCES AVAILABILITY OF ANNUAL LETTER TO SHAREHOLDERS Itasca, Illinois (March 2, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that a letter to its shareholders from John T. Fitzgerald, the Company’s President and CEO, has been made available (the “Letter”). The Letter can be found on the Company’s website by following ei

February 28, 2020 EX-10.1

KINGSWAY ANNOUNCES EXECUTIVE TRANSITION

EX-10.1 2 exhibit101-kingswayannounc.htm EXHIBIT 10.1 Exhibit 10.1 KINGSWAY ANNOUNCES EXECUTIVE TRANSITION Itasca, Illinois (February 28, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) announced today that Kent A. Hansen has been named Chief Financial Officer of the Company, effective immediately, following the Board’s acceptance of the resignation of William A.

February 28, 2020 EX-10.2

Employment Offer Letter, dated as of October 23, 2019, by and between Kent A. Hansen and Kingsway America Inc.

EX-10.2 3 exhibit102-employmentoffer.htm EXHIBIT 10.2 Exhibit 10.2 October 23, 2019 Mr. Kent A. Hansen [email protected] RE: Employment Offer Letter Dear Kent: It is with great pleasure that I write to you today to extend this offer to join the team as an employee of Kingsway America Inc. (the “Company”). The following is a summary of the terms of the offer, which is contingent upon satisfac

February 28, 2020 8-K

Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

February 28, 2020 EX-10.3

Employment Separation Agreement and Release, dated as of February 28, 2020, by and between Kingsway America Inc. and William A. Hickey, Jr

EX-10.3 4 exhibit103-employmentsepar.htm EXHIBIT 10.3 Exhibit 10.3 EMPLOYMENT SEPARATION AGREEMENT AND RELEASE This EMPLOYMENT SEPARATION AGREEMENT AND RELEASE (“Agreement”) is made and entered into by and between Kingsway America Inc., a Delaware corporation (“Employer”), and William A. Hickey, Jr., an individual residing in the State of Illinois (“Employee”). WITNESSETH: WHEREAS, Employee and Em

February 28, 2020 EX-10.4

Consulting Agreement, dated as of February 28, 2020, by and between Kingsway America Inc. and William A. Hickey, Jr.

Exhibit 10.4 CONSULTING AGREEMENT This CONSULTING AGREEMENT (“Agreement”), dated as of the 28th day of February 2020 (the “Effective Date”), is made and entered into by and between William A. Hickey, Jr., an individual residing in the State of Illinois (“Consultant”), and Kingsway America Inc., a Delaware corporation (the “Company”). RECITALS WHEREAS, Consultant was previously employed by the Comp

February 28, 2020 EX-99.1

KINGSWAY PROVIDES FURTHER UPDATE ON 2018 FORM 10-K FILING

EX-99.1 6 exhibit99122820.htm EXHIBIT 99.1 Exhibit 99.1 KINGSWAY PROVIDES FURTHER UPDATE ON 2018 FORM 10-K FILING Itasca, Illinois (February 27, 2020) - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today filed its Annual Report on Form 10-K for the fiscal year ended December 31, 2018. The Company also filed today amended Forms 10-Q/A for the quarters ended March 31, 2

February 27, 2020 10-Q/A

KFS / Kingsway Financial Services Inc. 10-Q/A - Quarterly Report - 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fin

February 27, 2020 10-Q/A

KFS / Kingsway Financial Services Inc. 10-Q/A - Quarterly Report - 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingsway Fi

February 27, 2020 EX-21

Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21 Subsidiaries of Kingsway Financial Services Inc. Subsidiaries Jurisdiction of Incorporation/Organization Kingsway America II Inc. Delaware 1347 Advisors LLC Delaware 1347 Capital LLC Delaware Itasca Investors LLC Delaware Itasca Capital Corp. Delaware 1347 Venture Opportunity LLC Delaware American Country Underwriting Agency Inc. Illinois Argo Management Group, LLC Delaware ARM Holdings

February 27, 2020 10-K

KFS / Kingsway Financial Services Inc. 10-K - Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number 001-15204 Kingsway Financial Service

February 27, 2020 10-Q/A

KFS / Kingsway Financial Services Inc. 10-Q/A - Quarterly Report - 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from to Commission File Number: 001-15204 Kingswa

January 15, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 15, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

January 14, 2020 8-K/A

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 6, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

January 10, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 6, 2020 KINGSWAY FINANCIAL SERVICES INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or Other Jurisdiction of Incorporation) 001-15204 (Commission

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