Lemonade officer plans sale of 1,040 shares

An officer of Lemonade, Inc. filed a Rule 144 notice to sell 1,040 common shares, partly to cover taxes on a vested equity award.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) is the issuer of common stock that an officer, Maya Prosor, has filed to sell under Rule 144. The notice covers a proposed sale of 1,040 shares of common stock held at Fidelity Brokerage Services LLC, with an aggregate value of $56,816.24.

The filing also reports that during the prior three months, Maya Prosor sold 1,220 shares of Lemonade common stock for $64,871.30

Key Figures

Shares proposed to be sold: 1,040 shares Aggregate value of proposed sale: $56,816.24 Shares sold in past 3 months: 1,220 shares +3 more

6 metrics

Shares proposed to be sold 1,040 shares Common stock under current Rule 144 notice for Maya Prosor

Aggregate value of proposed sale $56,816.24 Value listed for 1,040 Lemonade, Inc. common shares

Shares sold in past 3 months 1,220 shares Common stock sales by Maya Prosor during prior three months

Aggregate value of past 3 months’ sales $64,871.30 Value of 1,220 Lemonade, Inc. common shares sold previously

Date of Notice September 3, 2026 Date the Form 144 notice was filed

Date of restricted stock vesting September 1, 2026 Event giving rise to the securities to be sold

Key Terms

Rule 144, Restricted Stock Vesting, equity award distribution, tax obligation

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Restricted Stock Vesting financial

"Common | 09/01/2026 | Restricted Stock Vesting | Issuer"

Restricted stock vesting is the timetable and conditions under which shares granted to employees or insiders become fully owned and can be sold, typically requiring continued work or meeting performance goals. It matters to investors because large blocks of shares can become tradable at once, which can change share supply and price, and because vesting aligns insiders’ incentives with the company’s long‑term performance—think of it like a timed unlock that both rewards and locks in key people.

equity award distribution financial

"resulting from the settlement of a vested equity award distribution."

tax obligation financial

"Sale includes an amount necessary to cover a tax obligation"

FAQ

What does the Form 144 filing for LMND disclose about planned stock sales?

The Form 144 reports that officer Maya Prosor intends to sell 1,040 shares of Lemonade, Inc. common stock. The shares are held at Fidelity Brokerage Services LLC, and the aggregate value listed for this proposed sale is $56,816.24.

Who is selling Lemonade, Inc. (LMND) shares in this Form 144 notice?

The seller is Maya Prosor, identified as an officer of Lemonade, Inc. The notice states that the sale is for her account and that part of the shares relate to a vested equity award settlement and associated tax obligations.

How many LMND shares has the officer sold in the past three months?

Over the past three months, 1,220 shares of Lemonade, Inc. common stock were sold for an aggregate amount of $64,871.30. These prior sales are reported in the same Form 144 filing for Maya Prosor.

What is the purpose of part of the LMND shares being sold under this Form 144?

The remark states that the sale includes an amount of shares necessary to cover a tax obligation resulting from the settlement of a vested equity award distribution, indicating that some of the shares are being sold to satisfy related taxes.

When was the Form 144 notice for Lemonade, Inc. (LMND) filed?

The Date of Notice on the Form 144 for Lemonade, Inc. is September 3, 2026. The securities to be sold are tied to restricted stock vesting dated September 1, 2026.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/03/2026 - 03:33 PM Accepted by SEC EDGAR 09/03/2026 - 03:32 PM Learn about SEC filing dates

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	1040	56816.24	77396615	09/03/2026	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	09/01/2026	Restricted Stock Vesting	Issuer			1040	09/01/2026	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	06/03/2026	1220	64871.30

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	09/03/2026
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/ Jessica Spraker, 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)