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Lemonade, Inc. insider sale to cover tax withholding on vested RSUs. John Sheldon Peters, Chief Insurance Officer, reported a non-discretionary sale of 2,718 shares of Lemonade common stock on 09/03/2025 at a price of $50.34 per share to satisfy tax withholding obligations tied to the vesting and settlement of Restricted Stock Units. After the transaction he beneficially owned 102,397 shares. The Form 4 was signed by an attorney-in-fact on behalf of the reporting person on 09/05/2025. The filing states the sale was not discretionary and solely to cover taxes.

Timothy E. Bixby, Chief Financial Officer and Director of Lemonade, Inc. (LMND), reported a non-discretionary sale of 2,906 shares of Lemonade common stock on 09/03/2025 at a price of $50.34 per share to cover tax withholding obligations arising from the vesting and settlement of restricted stock units. After the transaction he beneficially owned 260,487 shares directly and 30,000 shares indirectly through the Timothy E Bixby Family Trust, for which he is co-trustee with voting and dispositive control. The Form 4 is signed and dated 09/05/2025.

Lemonade, Inc. (LMND) Form 144 filed a notice to sell 2,906 common shares valued at $146,294.73 (based on the aggregate market value reported) with an approximate sale date of 09/03/2025. The shares were acquired on 08/29/2025 by restricted stock vesting from the issuer and were paid as compensation. The filing shows 73,916 common shares were sold by Timothy E. Bixby during the prior three months for aggregate gross proceeds of $3,072,290.92, with individual sales between 06/03/2025 and 07/21/2025. The filer certifies no undisclosed material adverse information and acknowledges legal penalties for misstatement.

Form 144 notice for Lemonade, Inc. (LMND): The filer reports a proposed sale of 282 common shares through Fidelity Brokerage Services with an aggregate market value of $14,196.53. The shares were acquired via restricted stock vesting on 08/29/2025 and payment was recorded as compensation on the same date. The approximate sale date is listed as 09/03/2025 and the securities trade on the NYSE. The filing shows 73,886,417 shares outstanding. The filer also disclosed a prior sale on 06/03/2025 of 252 shares for $8,883.25. The notice includes the required representation that the seller is not aware of undisclosed material adverse information.

Lemonade, Inc. (LMND) filing a Form 144 reports proposed sale of restricted common stock by an insider. The notice states 2,718 shares held at Fidelity Brokerage will be offered with an aggregate market value of $136,830.37, and an approximate sale date of 09/03/2025 on the NYSE. The shares were acquired by restricted stock vesting on 08/29/2025 and received as compensation. The filing lists prior sales by the same person within three months: 1,494 shares (06/03/2025), 6,543 shares (06/23/2025), and 38,155 shares (08/13/2025) with gross proceeds shown.

Shai Wininger, President and Director of Lemonade, Inc. (LMND), received a grant of stock options covering 127,780 shares with an exercise price of $59.74. The option award was reported as a transaction dated 08/21/2025 and the form was signed on 08/25/2025 by an attorney-in-fact. The filing states the option will vest in 12 equal quarterly installments beginning on 08/18/2025, subject to continued employment, and the option expires on 08/18/2035. After the reported grant, the reporting person beneficially owns 127,780 shares directly attributable to this option position.

Adina Eckstein, Chief Operating Officer of Lemonade, Inc. (LMND), was granted 38,334 restricted stock units on 08/21/2025. Each restricted stock unit represents a contingent right to receive one share of Lemonade common stock and will vest in 12 equal quarterly installments beginning August 1, 2025, subject to the reporting person's continued employment through each vesting date. After the reported grant, the filing shows the reporting person beneficially owns 227,987 shares of common stock. The Form 4 was signed by Timothy Bixby as attorney-in-fact on 08/25/2025.

Daniel A. Schreiber, Chief Executive Officer and Director of Lemonade, Inc. (LMND), was granted a stock option on 08/21/2025 covering 127,780 underlying shares with an exercise price of $59.74. The option is exercisable in 12 equal quarterly installments beginning 08/18/2025 and expires 08/18/2035, and the shares are reported as directly owned. Following the reported grant, the filing shows 127,780 common shares underlying the option beneficially owned by the reporting person. The grant is subject to continued employment through each vesting date.

John Sheldon Peters, Chief Insurance Officer of Lemonade, Inc. (LMND), was granted a stock option covering 25,556 shares with an exercise price of $59.74. The reported transaction date is 08/21/2025 and the Form 4 was filed on 08/25/2025. The option vests in 12 equal quarterly installments beginning 08/18/2025 and becomes exercisable according to that schedule, with an expiration date of 08/18/2035. After this grant, the reporting person directly beneficially owns 25,556 common shares (from this option) at a stated price of $0 for the reported beneficial ownership figure. The form was signed by an attorney-in-fact on behalf of the reporting person.