| 2026-08-06 | 10-Q | 10.2 | Director Retainer Agreement, dated as of May 18, 2026, by and between Kingsway Corporation and Adam Patinkin. |
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| 2026-05-11 | 8-K | 10.1 | Membership Interest Purchase Agreement, dated May 8, 2026, by and between Kingsway Warranty Holdings LLC and Trinity Warranty Holding LLC. |
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| 2025-07-07 | 8-K | 10.2 | Credit Agreement, dated July 1, 2025, by and between Roundhouse Electric & Equipment Co., Inc., Longhorns Acquisition LLC and Main Street Bank.* |
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| 2025-07-07 | 8-K | 10.1 | Stock Purchase Agreement, dated July 1, 2025, by and among Longhorns Acquisition LLC, Armando Gonzales and Lee Hudson.* |
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| 2025-06-25 | 8-K | 10.1 | Stock Purchase Agreement, dated June 24, 2025, by and among the Company and the purchasers named therein. |
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| 2025-05-19 | 8-K | 10.2 | Form of Subscription Agreement – Individual Investor |
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| 2025-05-19 | 8-K | 10.1 | Form of Subscription Agreement – Legal Entity |
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| 2025-02-18 | 8-K | 10.2 | FORM OF SUBSCRIPTION AGREEMENT - INDIVIDUAL INVESTOR |
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| 2025-02-18 | 8-K | 10.1 | FORM OF SUBSCRIPTION AGREEMENT - LEGAL ENTITY |
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| 2024-09-27 | 8-K | 10.4 | Credit Agreement, dated as of September 26, 2024, between Image Solutions, LLC, Steel Bridge Acquisition LLC and Avidbank* |
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| 2024-09-27 | 8-K | 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* |
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| 2024-09-27 | 8-K | 10.2 | Form of Subscription Agreement – Individual Investor |
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| 2024-09-27 | 8-K | 10.1 | Form of Subscription Agreement – Legal Entity |
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| 2024-05-29 | 8-K | 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. |
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| 2023-10-30 | 8-K | 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*. |
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| 2023-10-23 | 8-K | 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*. |
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| 2023-03-08 | 10-K | 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. |
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| 2022-12-23 | 8-K | 10.1 | PURCHASE AND SALE AGREEMENT DATED DECEMBER 22, 2022, BY AND BETWEEN TRT LEASECO, LLC, AS SELLER, AND BNSF DAYTON LLC, AS PURCHASER |
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| 2022-11-21 | 8-K | 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 * |
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| 2022-11-02 | 8-K | 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* |
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| 2021-10-04 | 8-K | 10.1 | 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 |
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| 2021-04-02 | 8-K | 10.1 | EMPLOYMENT SEPARATION AGREEMENT AND RELEASE, BY AND BETWEEN KINGSWAY AMERICA, INC. AND PAUL R. HOGAN, DATED AS OF MARCH 31, 2021 |
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| 2021-03-29 | 10-K | 10.29 | Form of Restricted Stock Agreement. * |
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| 2021-03-29 | 10-K | 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. |
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| 2020-12-02 | 8-K | 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 * |
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| 2020-02-28 | 8-K | 10.4 | Consulting Agreement, dated as of February 28, 2020, by and between Kingsway America Inc. and William A. Hickey, Jr. |
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| 2020-02-28 | 8-K | 10.3 | Employment Separation Agreement and Release, dated as of February 28, 2020, by and between Kingsway America Inc. and William A. Hickey, Jr. |
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| 2020-02-28 | 8-K | 10.2 | Employment Offer Letter, dated as of October 23, 2019, by and between Kent A. Hansen and Kingsway America Inc. |
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| 2020-02-28 | 8-K | 10.1 | Press Release Titled “Kingsway Announces Executive Transition” |
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| 2019-02-14 | 8-K | 10.2 | Advisor Agreement, dated January 31, 2019, between Kingsway America Inc. and Sequoia Financial LLC |
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| 2019-02-14 | 8-K | 10.1 | Employment Separation Agreement and Release, dated January 31, 2019, between Kingsway America Inc. and Hassan R. Baqar |
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| 2018-11-09 | 10-Q | 10.9 | Letter Agreement, dated May 30, 2018, between the Company and Larry Swets |
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| 2018-09-10 | 8-K | 10.9 | Membership Interest Purchase Agreement, dated September 5, 2018, between 1347 Capital LLC and IGI Partners, LLC |
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| 2018-09-10 | 8-K | 10.8 | Amended and Restated Restricted Stock Agreement, dated September 5, 2018, between the Company and Larry G. Swets, Jr. |
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| 2018-09-10 | 8-K | 10.7 | Senior Advisor Agreement, dated September 5, 2018, between Kingsway America Inc. and Larry G. Swets, Jr. |
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| 2018-09-10 | 8-K | 10.6 | Separation Agreement and Release, dated September 5, 2018, between Kingsway America Inc. and Larry G. Swets, Jr. |
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| 2018-09-10 | 8-K | 10.5 | Form of Indemnification Agreement for Directors and Officers |
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| 2018-09-10 | 8-K | 10.4 | Restricted Stock Agreement, dated September 5, 2018, between the Company and John T. Fitzgerald |
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| 2018-09-10 | 8-K | 10.3 | Severance Agreement, dated September 5, 2018, between the Company and John T. Fitzgerald |
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| 2018-09-10 | 8-K | 10.2 | Offer Letter, dated September 5, 2018, between the Company and John T. Fitzgerald |
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| 2018-09-10 | 8-K | 10.1 | Press Release, dated September 5, 2018 |
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| 2018-08-08 | 10-Q | 10.1 | Amendment No. 1 to the Kingsway Financial Services Inc. 2013 Equity Incentive Plan |
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| 2016-11-16 | 8-K | 10.7 | Right of First Offer Agreement, dated as of November 16, 2016 by and between the Company and W.H.I. Growth Fund Q.P., L.P. |
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| 2016-11-16 | 8-K | 10.6 | Right of First Offer Agreement, dated as of November 16, 2016 by and between the Company and GrizzlyRock Institutional Value Partners, LP. |
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| 2016-11-16 | 8-K | 10.5 | Registration Rights Agreement, dated as of November 16, 2016 by and between the Company and Yorkmont Capital Partners, LP. |
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| 2016-11-16 | 8-K | 10.4 | Registration Rights Agreement, dated as of November 16, 2016 by and among the Company, GrizzlyRock Institutional Value Partners, LP and W.H.I. Growth Fund Q.P., L.P. |
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| 2016-11-16 | 8-K | 10.3 | Stock Purchase Agreement, dated as of November 9, 2016 by and between the Company and Yorkmont Capital Partners, LP. |
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| 2016-11-16 | 8-K | 10.2 | Stock Purchase Agreement, dated as of November 9, 2016 by and between the Company and W.H.I. Growth Fund Q.P., L.P. |
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| 2016-11-16 | 8-K | 10.1 | Stock Purchase Agreement, dated as of November 9, 2016 by and between the Company and GrizzlyRock Institutional Value Partners, LP. |
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| 2016-08-04 | 10-Q | 10.5 | Lease between TRT LeaseCo, LLC, as Landlord, and BNSF Railway Company (f/k/a The Burlington Northern and Santa Fe Railway Company), as Tenant, dated as of June 1, 2014. |
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| 2016-08-04 | 10-Q | 10.4 | Deed of Trust, Security Agreement, Assignment of Leases and Rents and Fixture Filing Statement, dated as of March 12, 2015, from TRT LeaseCo, LLC to Malcolm Morris, as Deed of Trust Trustee for the benefit of Wells Fargo Bank Northwest, N.A., as trustee. |
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| 2016-08-04 | 10-Q | 10.3 | TRT LeaseCo, LLC 4.07% Senior Secured Note, Due May 15, 2034. |
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| 2016-07-20 | 8-K | 10.2 | Management Services Agreement, dated as of July 14, 2016, by and between TRT LeaseCo, LLC and DGI-BNSF Corp. |
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| 2016-07-20 | 8-K | 10.1 | Stockholders’ Agreement, dated as of July 14, 2016, by and between CMC Industries, Inc., CMC Acquisition LLC and CRIC TRT Acquisition LLC. |
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| 2015-02-27 | 8-K | 10.1 | Agreement to Buyout and Release dated February 24, 2015 between 1347 Advisors LLC and 1347 Property Insurance Holdings, Inc. |
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| 2014-02-04 | 8-K | 10.2 | Registration Rights Agreement, dated February 3, 2014, by and among the Company and the other parties signatory thereto |
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| 2013-12-27 | 8-K | 10.2 | Form of Registration Rights Agreement |
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| 2013-12-27 | 8-K | 10.1 | Form of Subscription Agreement |
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| 2013-09-19 | 8-K | 10.2 | Common Stock Series B Warrant Agreement |
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| 2013-09-19 | 8-K | 10.1 | Common Stock Series A Warrant Agreement |
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| 2012-03-30 | 10-K | 10.5 | AGREEMENT AND PLAN OF MERGER |
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| 2012-03-30 | 10-K | 10.4 | TAX BENEFIT PRESERVATION PLAN AGREEMENT BETWEEN KINGSWAY FINANCIAL SERVICES INC. AND COMPUTERSHARE INVESTOR SERVICES INC. |
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| 2012-03-30 | 10-K | 10.3 | SECOND AMENDMENT TO AND ASSIGNMENT AND ASSUMPTION OF PURCHASE AGREEMENT |
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| 2012-03-30 | 10-K | 10.2 | PURCHASE AGREEMENT BETWEEN THE WESTAIM CORPORATION AND KINGSWAY FINANCIAL SERVICES INC. |
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| 2012-03-30 | 10-K | 10.1 | AMENDED AND RESTATED STOCK OPTION PLAN |
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| 2012-03-28 | 10-Q | 10.9 | SUBSCRIPTION AND INVESTMENT REPRESENTATION AGREEMENT |
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| 2012-03-28 | 10-Q | 10.8 | OPERATING AGREEMENT OF ACADIA GP, LLC |
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| 2012-03-28 | 10-Q | 10.7 | INTERCREDITOR AGREEMENT BETWEEN HRM ACQUSITION CORP. AND KINGSWAY AMERICA INC. |
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| 2012-03-28 | 10-Q | 10.6 | AGREEMENT OF LIMITED PARTNERSHIP BETWEEN ACADIA GP, LLC AND LIMITED PARTNERS |
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| 2012-03-28 | 10-Q | 10.5 | PROMISSORY NOTE ISSUED BY HRM ACQUISITION CORP. TO UNITED |
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| 2012-03-28 | 10-Q | 10.4 | NOTE PURCHASE AGREEMENT BETWEEN HRM ACQUISITION CORP. TO UNITED |
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| 2012-03-28 | 10-Q | 10.3 | JUNIOR PROMISSORY NOTE ISSUED BY HRM ACQUISITION CORP. TO KINGSWAY AMERICA INC. |
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| 2012-03-28 | 10-Q | 10.2 | SENIOR PROMISSORY NOTE ISSUED BY HRM ACQUISITION CORP. TO KINGSWAY AMERICA INC. |
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| 2012-03-28 | 10-Q | 10.1 | STOCK PURCHASE AGREEMENT BETWEEN HRM AQUISITION CORP. AND KINGSWAY AMERICA INC. |
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| 2012-03-28 | 10-Q | 10.1 | MANAGEMENT SERVICES AGREEMENT |
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