Sec Form 4 Filing - Ilany Jonathan @ TIPTREE INC. - 2025-09-15

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Ilany Jonathan 2. Issuer Name and Ticker or Trading Symbol TIPTREE INC. [ TIPT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Executive Officer (Last) (First) (Middle) C/O TIPTREE INC., 660 STEAMBOAT ROAD 3. Date of Earliest Transaction (MM/DD/YY) 09/15/2025 (Street) GREENWICH, CT06830 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 09/15/2025 M( 1 ) 351,155 A $ 6.65 498,060 D Common Stock 09/15/2025 F( 2 ) 98,531 D $ 23.7 ( 3 ) 399,529 D Common Stock 09/15/2025 F( 4 ) 124,787 D $ 23.7 ( 3 ) 274,742 D Common Stock 192,021 I By 401K

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Employee Stock Option ( 5 ) $ 6.65 09/15/2025 M 351,155 02/22/2017( 6 ) 02/22/2027 Common Stock 351,155 $ 6.65 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Ilany Jonathan C/O TIPTREE INC. 660 STEAMBOAT ROAD GREENWICH, CT06830 X Chief Executive Officer Signatures /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany 09/17/2025 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed. ( 2 )Reflects 98,531 shares withheld by the Issuer at the market price of $23.70 per share less an exercise price of $6.65 per share to fund the cashless exercise of 351,155 options. ( 3 )Represents the closing stock price as of the transaction date. ( 4 )Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless calculated at the closing stock price of the exercise date. ( 5 )On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 351,155 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement. ( 6 )The option shares are fully vested and exercisable as of February 22, 2022.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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