TIPTREE INC.

For information regarding factors that could affect the Company’s results of operations and financial condition, see the risk factors discussed under Part I, Item 1A in Tiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025. Except as set forth below, there have been no material changes in those risk factors.

Following the Sale of Fortegra, we are relying on a temporary exclusion from registration under the Investment Company Act of 1940.

Following the Sale of Fortegra on May 29, 2026, we hold significant cash, cash equivalents and investments pending deployment of capital. As a result, we are currently relying on Rule 3a-2 under the Investment Company Act of 1940, which provides a temporary exclusion from investment company registration for issuers that temporarily hold investment securities while pursuing a business other than investing in securities.

Rule 3a-2 is available only for a limited period and requires us to satisfy the conditions of the rule within the applicable timeframe. If we are unable to deploy capital, complete acquisitions or other strategic transactions, or otherwise manage our assets in a manner that permits us to continue to qualify for an exclusion or exemption from registration under the Investment Company Act of 1940, we could be required to register as an investment company or take other actions that could adversely affect our business, financial condition and strategic objectives.

Registration under the Investment Company Act of 1940 would subject us to substantial regulatory requirements and restrictions regarding, among other things, our operations, capital structure, transactions with affiliates and investment activities, which could materially and adversely affect our business, financial condition and results of operations. We cannot assure investors that suitable acquisition or other capital deployment opportunities will be available on acceptable terms or within the period required to maintain our exclusion from investment company registration.