Results of Operations and Financial Condition. On July 29, 2026 Tiptree issued a press release announcing its results of operations for the six months ended June 30, 2026. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement of the proposed Transaction, a copy of which is furnished as Exhibit 99.1 and incorporated herein by reference. Also included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of August 17, 2026 and a payment date of August 24, 2026. The inf…

Entry into a Material Definitive Agreement. On July 28, 2026, Tiptree Inc. (“Tiptree”), entered into a Stock Purchase Agreement (the “Purchase Agreement”) with Shield Holdings, LLC, UH Partners, LLC, certain individual equityholders identified therein (collectively, the “Sellers”), and the Sellers’ Representative (as defined therein). Pursuant to the Purchase Agreement, Tiptree agreed to acquire all of the issued and outstanding equity interests of Universal Shield Insurance Group, Inc. (“USI…

Other Events. On May 29, 2026, Tiptree issued a press release announcing the Closing of the Merger. A copy of the press release is filed as Exhibit 99.1 to this Current Report and is incorporated herein by reference.

Completion of Acquisition or Disposition of Assets. As disclosed in the Current Report on Form 8-K filed by Tiptree with the Securities and Exchange Commission (the “ SEC ”) on September 26, 2025 (the “ September 26 Current Report ”), on September 26, 2025, Tiptree entered into an Agreement and Plan of Merger (as amended, the “ Merger Agreement ”) with Purchaser, and Fortegra. DB Insurance North America Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Purchaser (“ Merge…

Termination of a Material Definitive Agreement. On the Closing Date, in connection with the Merger, Tiptree Holdings LLC (“ Tiptree Holdings ”), a subsidiary of Tiptree, repaid in full all outstanding obligations under the Credit Agreement, dated as of February 7, 2025 (the “ Fortress Credit Agreement ”), by and among Tiptree, as parent, Tiptree Holdings, the lenders party thereto and Fortress Credit Corp., as administrative agent and collateral agent. After giving effect to such repayment, a…

Entry into a Material Definitive Agreement. In connection with the closing of the Merger (as defined in

Completion of Acquisition or Disposition of Assets. On May 1, 2026, Tiptree Inc. (“Tiptree”) and Reliance Holdings LLC (“Holdings”), a wholly owned subsidiary of Tiptree, as sellers (the “Sellers”) completed the sale (the “Sale”) of all of the issued and outstanding membership interests of Reliance First Capital LLC (“Reliance”), a wholly owned subsidiary of Holdings to Carrington Mortgage Services, LLC, as buyer (the “Buyer”) pursuant to the Purchase Agreement, dated October 31, 2025 as amen…

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of May 18, 2026 and a payment date of May 26, 2026. On April 30, 2026, the Company posted an investor presentation dated April 2026 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to this Form 8…

Entry into a Material Definitive Agreement. On April 28, 2026, Tiptree Inc., a Maryland corporation (“ Tiptree ” or the “ Company ”), The Fortegra Group, Inc., a Delaware corporation and subsidiary of the Company (“ Fortegra ”), DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea (“ Purchaser ”), and DB Insurance North America Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Purchaser (“ Merger Sub ”), entered into that certain Firs…

Results of Operations and Financial Condition. On April 30, 2026 Tiptree issued a press release announcing its results of operations for the three months ended March 31, 2026. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of March 16, 2026 and a payment date of March 23, 2026. On March 6, 2026, the Company posted an investor presentation dated March 2026 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to this For…

Results of Operations and Financial Condition. On March 6, 2026 Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the twelve months ended December 31, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Chief Executive Officer — Jonathan Ilany: Jonathan Ilany is transitioning from CEO to non-executive Vice Chairman with a consulting agreement.

Vice President, General Counsel and Secretary — Neil Rifkind: Tiptree separated from Neil Rifkind as Vice President, General Counsel and Secretary due to downsizing its legal department.

Results of Operations and Financial Condition. On October 31, 2025, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the nine months ended September 30, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Entry into a Material Definitive Agreement. On October 31, 2025, Tiptree Inc. (“Tiptree”), entered into a Purchase Agreement, dated as of October 31, 2025 (the “Purchase Agreement”) by and among Carrington Holding Company, LLC, as buyer (the “Buyer”), Tiptree and Reliance Holdings LLC (“Holdings”), a wholly owned subsidiary of Tiptree, as sellers (the “Sellers”) and Reliance First Capital, LLC, a wholly owned subsidiary of Holdings (“Reliance”). Pursuant to the Purchase Agreement, the Buyer w…

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of November 17, 2025 and a payment date of November 24, 2025. On October 31, 2025, the Company posted an investor presentation dated October 31, 2025 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 9…

Entry into a Material Definitive Agreement. The Merger Agreement On September 26, 2025, Tiptree Inc., a Maryland corporation (“ Tiptree ”), entered into an Agreement and Plan of Merger (the “ Merger Agreement ”) with DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea (“ Purchaser ”), and The Fortegra Group, Inc., a Delaware corporation and subsidiary of Tiptree (“ Fortegra ”). A subsidiary of Purchaser (“ Merger Sub ”) to be incorporated in Delaware foll…

Results of Operations and Financial Condition. On July 30, 2025, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the quarter ended June 30, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of August 18, 2025 and a payment date of August 25, 2025 . On July 30, 2025 , the Company posted an investor presentation dated July 30, 2025 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to t…

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of May 12, 2025 and a payment date of May 19, 2025 . On April 30, 2025 , the Company posted an investor presentation dated April 30, 2025 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to this…

Results of Operations and Financial Condition. On April 30, 2025, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the quarter ended March 31, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Results of Operations and Financial Condition. On February 26, 2025, Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the quarter ended December 31, 2024. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Regulation FD Disclosure. Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of March 10, 2025 and a payment date of March 17, 2025 . On February 26, 2025 , the Company posted an investor presentation dated February 26, 2025 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.…