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Timothy E. Bixby, Chief Financial Officer of Lemonade, Inc. (LMND), was granted a stock option on 08/21/2025 for 127,780 shares with an exercise price of $59.74 per share. The option vests in 12 equal quarterly installments beginning on 08/18/2025 and expires on 08/18/2035. The report indicates the shares underlying the option total 127,780 common shares and are listed as directly beneficially owned following the transaction. Vesting is conditioned on the reporting person鈥檚 continued employment through each vesting date. The Form 4 is signed by Mr. Bixby on 08/25/2025.

John Peters, Chief Insurance Officer at Lemonade, Inc. (LMND), reported multiple transactions affecting his beneficial ownership. The filing shows a charitable donation of 1,000 common shares on 08/12/2025 with no value received. On 08/13/2025 he acquired 38,155 common shares by exercising a fully vested stock option at an exercise price of $11.61 per share. The same day he sold 38,155 common shares pursuant to a Rule 10b5-1 trading plan at a sale price of $60.00 per share. Following these transactions his reported beneficial ownership is 105,115 shares.

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported option exercise and a contemporaneous sale on 08/13/2025. She exercised 5,000 stock options at an exercise price of $24.47 and immediately sold 5,000 common shares at $58.00 per share pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024. The option exercised is fully vested. After these transactions, Ms. Eckstein beneficially owned 189,653 shares. The Form 4 was signed by an attorney-in-fact on her behalf on 08/15/2025.

The Form 144 filed for Lemonade, Inc. (LMND) reports a proposed sale of 5,000 common shares through Oppenheimer & Co. on the NYSE with an aggregate market value of $272,950. The shares were acquired on 06/07/2020 under an employee stock option plan and are to be paid in cash upon exercise on 08/13/2025. Outstanding shares are listed as 73,886,417, so the proposed sale equals roughly 0.0068% of outstanding stock. The filing also discloses three prior sales by the same person totaling 15,000 shares for $735,000 on 06/23/2025, 08/05/2025, and 08/11/2025. Signature and notice date fields are not shown in the provided content.

SoftBank Group Capital Ltd reports direct beneficial ownership of 5,958,698 shares of Lemonade, Inc. That holding represents 8.1% of Lemonade's common stock based on 73,266,170 shares outstanding as disclosed by the issuer. The Reporting Person states it has sole voting and sole dispositive power over these shares.

The filing also references the issuer's charter provision that any positive excess votes above 9.90% would be distributed pro rata to other stockholders; the disclosed position is below that threshold. The disclosure is a Schedule 13G amendment reporting ownership and voting/dispositive authority only.

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), reported transactions on Form 4 dated 08/11/2025. The filing discloses a sale of common stock executed pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024, with a reported sale price of $53. Following the reported transactions, Ms. Eckstein beneficially owns 189,653 shares of common stock.

The filing also reports a derivative entry for a stock option with an exercise/conversion price of $24.47 covering 5,000 underlying shares and shows 21,250 derivative securities beneficially owned following the transactions; the option is stated to be fully vested. The form was signed by an attorney-in-fact on 08/13/2025.

Lemonade, Inc. (LMND) filed a Form 144 disclosing a proposed sale of 38,155 shares of common stock through Fidelity Brokerage Services LLC (900 Salem Street, Smithfield, RI) on the NYSE with an aggregate market value of $2,289,300.00. The company shows 73,886,417 shares outstanding, so the proposed sale equals about 0.052% of outstanding shares.

The securities are reported as acquired under an option granted 02/06/2019, with the acquisition and planned sale dated 08/13/2025, and payment noted as cash. The filing also lists two prior sales by John Peters in the past three months: 1,494 shares on 06/03/2025 for $52,664.98 and 6,543 shares on 06/23/2025 for $294,435.00. Other filer and notice administrative fields are not populated in the provided content.

Lemonade insider Adina Eckstein filed a Form 144 notifying a proposed sale of 5,000 common shares to be executed through Oppenheimer & Co. on 08/11/2025 with an aggregate market value of $244,900. The shares were acquired on 06/07/2020 under an employee stock option plan and will be paid in cash upon exercise. The filing lists 73,886,417 shares outstanding, making the proposed block about 0.0068% of outstanding stock. The filer disclosed two recent sales in the past three months totaling 10,000 shares for $470,000 in gross proceeds. The notice includes the standard representation that the filer is not aware of any undisclosed material adverse information.