TIPT · Tiptree Inc.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

This purchase was executed in multiple purchases at prices ranging from $15.94 to $16.00, inclusive. The price reported above reflects the weighted average price. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transaction was effected.

This purchase was executed in multiple purchases at prices ranging from $16.10 to $16.20, inclusive. The price reported above reflects the weighted average price. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transaction was effected.

The acquisition of the common stock resulted from the cliff vesting of matching restricted stock units ("RSUs") granted to the Reporting Person on February 22, 2023.

Represents the cliff vesting of matching RSUs which were granted to the Reporting Person on February 22, 2023.

Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the RSUs.

Represents the closing stock price as of the transaction date.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

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.

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.

The option shares are fully vested and exercisable as of February 22, 2022.

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.

Represents the closing stock price as of the transaction date.

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.

Represents the closing stock price as of the transaction date.

On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 112,015 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement.

The option shares are fully vested and exercisable as of February 22, 2022.

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.

On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 46,494 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement.

The option shares are fully vested and exercisable as of January 4, 2021.

On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 4,649 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement.

The option shares are fully vested and exercisable as of March 10, 2021.

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.

Reflects 29,224 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $6.65 per share to fund the cashless exercise of 112,015 options.

Represents the closing stock price as of the transaction date.

Reflects 10,343 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.67 per share to fund the cashless exercise of 46,494 options.

Represents the closing stock price as of the transaction date.

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.

Reflects 1,071 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.87 per share to fund the cashless exercise of 4,649 options.

Represents the closing stock price as of the transaction date.

Reflects 33,262 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.67 per share to fund the cashless exercise of 137,038 options.

Represents the closing stock price as of the transaction date.

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.

Represents the closing stock price as of the transaction date.

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.

On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 137,038 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement.

The option shares are fully vested and exercisable as of January 4, 2021.

Reflects 3,444 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.87 per share to fund the cashless exercise of 13,704 options.

Represents the closing stock price as of the transaction date.

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.

On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 13,704 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement.

The option shares are fully vested and exercisable as of March 10, 2021.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

At the director's request, all director fees issued in shares are to be deposited into The Paul M. Friedman Living Trust dated 3/5/2019 (the "Living Trust"), of which the Reporting Person and his spouse are trustees.

Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of shares.

Represents the closing stock price as of the transaction date.

The Reporting Person was granted 11,123 matching restricted stock units on February 25, 2025, which represent the right to receive 2 shares of the Issuer's Common Stock for each restricted stock unit, pursuant to the Issuer's Equity Plan. As such the total in boxes 5 and 7 reflects the grant of 22,246 shares of the Issuer's Common Stock upon cliff vesting on February 28, 2028, subject to continuous employment from the grant date until such date and subject to certain terms contained in the Reporting Person's award agreement.

The acquisition of the common stock resulted from the cliff vesting of matching restricted stock units ("RSUs") granted to the Reporting Person on February 17, 2022.

Represents the cliff vesting of matching RSUs which were granted to the Reporting Person on February 17, 2022.

Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the RSUs.

Represents the closing stock price as of the transaction date.

Represents the cliff vesting of matching RSUs which were granted to the Reporting Person on February 17, 2022.

Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon vesting of the RSUs.

Represents the closing stock price as of the transaction date.

The acquisition of the common stock resulted from the cliff vesting of matching restricted stock units ("RSUs") granted to the Reporting Person on February 17, 2022.