Lemonade officer plans sale of 859 LMND shares

Lemonade officer John S. Peters filed a Rule 144 notice to sell 859 vested shares, partly to cover tax obligations from an equity award.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) was notified that officer John S. Peters intends to sell 859 shares of common stock under Rule 144 through Fidelity Brokerage Services LLC. The shares have an aggregate market value of $46,928.03 based on recent prices, out of 77,396,615 shares outstanding. The securities relate to restricted stock that vested on September 1, 2026, and the sale includes shares to cover a tax obligation arising from this equity award.

Key Figures

Shares planned for sale: 859 shares Aggregate market value of planned sale: $46,928.03 Shares outstanding: 77,396,615 shares +3 more

6 metrics

Shares planned for sale 859 shares Common stock to be sold under Rule 144 by John S. Peters

Aggregate market value of planned sale $46,928.03 Aggregate market value of the 859 LMND shares listed in the notice

Shares outstanding 77,396,615 shares Lemonade, Inc. common stock outstanding as reported in the filing

Sale on June 3, 2026 1,735 shares for $92,255.50 Common stock sold by John S. Peters during the past 3 months

Sale on August 13, 2026 11,000 shares for $578,000.38 Largest single disclosed sale in the past 3 months

Vesting date of restricted stock September 1, 2026 Acquisition date of the compensation-related restricted stock to be sold

Key Terms

Rule 144, restricted stock vesting, attorney-in-fact, 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.

attorney-in-fact regulatory

"as attorney-in-fact for John S. Peters"

An attorney-in-fact is the person or entity given legal authority through a power of attorney to act on behalf of another for specific tasks, such as signing documents, voting shares, or handling transactions. For investors, this matters because it lets a trusted representative make timely decisions or complete paperwork when the owner cannot, much like handing keys to someone to run errands on your behalf—so checks on scope and limits of that authority are important.

tax obligation financial

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

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does Lemonade, Inc. (LMND) disclose in this Form 144 filing?

The filing states that John S. Peters, an officer of Lemonade, Inc., plans to sell 859 shares of LMND common stock under Rule 144 through Fidelity Brokerage Services LLC, related to a recently vested restricted stock award and associated tax obligations.

How many Lemonade (LMND) shares are planned for sale and what is their value?

The notice reports an intended sale of 859 shares of Lemonade common stock with an aggregate market value of $46,928.03, as listed in the securities information section of the Form 144.

What is the source of the Lemonade (LMND) shares being sold by John S. Peters?

The shares come from restricted stock vesting on September 1, 2026, issued by Lemonade, Inc. The filing describes the nature of acquisition as compensation from the issuer.

Does the Form 144 for LMND mention tax-related share sales?

Yes. The remarks state that the sale includes an amount necessary to cover a tax obligation resulting from the settlement of a vested equity award distribution to John S. Peters.

What prior Lemonade (LMND) share sales by John S. Peters are disclosed?

Over the past three months, the filing lists sales on June 3, 2026 (1,735 shares for $92,255.50), June 4, 2026, July 6, 2026, and August 13, 2026, each involving common stock and reporting corresponding dollar amounts received.

How many Lemonade (LMND) shares are outstanding according to the Form 144?

The Form 144 reports that there are 77,396,615 shares of Lemonade, Inc. common stock outstanding, as shown in the securities information section.

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

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Available on EDGAR 09/03/2026 - 03:59 PM EDT Accepted by SEC EDGAR 09/03/2026 - 03:59 PM EDT 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	0001816299
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	Peters John Sheldon
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	859	46928.03	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			859	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
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2026	1735	92255.50
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/04/2026	3608	191007.52
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	07/06/2026	3444	272076.00
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	08/13/2026	11000	578000.38

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/ Adam Gehring, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for John S. Peters
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)