Lemonade, Inc. SEC Filing

Lemonade, Inc. insider plans small Rule 144 stock sale.

Accepted by SEC EDGAR 12/02/2025 - 04:16 PM EST Learn about SEC filing dates

Rhea-AI Filing Summary

Lemonade, Inc. insider plans small Rule 144 stock sale. A holder intends to sell 198 shares of Lemonade common stock through Fidelity Brokerage Services on 12/02/2025 on the NYSE, with an indicated aggregate market value of $14,401.49. These shares were acquired on 12/01/2025 through restricted stock vesting from the issuer as compensation.

The notice also reports that the same seller, Maya Prosor, sold 282 shares of Lemonade common stock on 09/03/2025 for gross proceeds of $14,196.53. The filer represents that they are not aware of any material adverse, nonpublic information about Lemonade’s current or prospective operations.

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Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0002011118
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Lemonade, Inc.
SEC File Number	001-39367
Address of Issuer	5 CROSBY STREET 3RD FLOOR NEW YORK NEW YORK 10013
Phone	(844) 733-8666
Name of Person for Whose Account the Securities are To Be Sold	Prosor Maya
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	198	14401.49	74731027	12/02/2025	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	12/01/2025	Restricted Stock Vesting	Issuer			198	12/01/2025	Compensation

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Maya Prosor 5 Crosby Street 3rd Floor New York NY 10013	Common	09/03/2025	282	14196.53

144: Remarks and Signature

Remarks	Sale includes an amount necessary to cover a tax obligation resulting from the settlement of a vested equity award distribution.
Date of Notice	12/02/2025
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Jennifer Ruchti, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Maya Prosor
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)