LMND insider files Form 144 to sell 3,608 shares

John S. Peters reported dispositions of Common Stock related to restricted‑stock vesting and a Form 144 sale notice.

Rhea-AI Filing Summary

John S. Peters reported dispositions of Common Stock related to restricted‑stock vesting and a Form 144 sale notice. The filing lists 3,608 shares tied to restricted stock vesting on 06/01/2026 and a Form 144 entry dated 06/04/2026 showing $191,007.52 for 3,608 shares through Fidelity Brokerage Services LLC. The filing also discloses prior sales in the past three months: 3,571 shares on 03/04/2026 for $187,477.50 and 1,735 shares on 06/03/2026 for $92,255.50.

Insights

Insider‑Transactions Analyst

Form 144 shows a notice to sell vested shares and records recent open‑market dispositions.

The filing ties 3,608 vested shares (06/01/2026) to a Form 144 sale notice (06/04/2026) with an aggregate value of $191,007.52, processed through Fidelity Brokerage Services LLC. Prior reported dispositions include 3,571 shares (03/04/2026) and 1,735 shares (06/03/2026).

Cash‑flow treatment and any trading plan are not stated in the excerpt; subsequent filings or trade confirmations would show execution details and timing.

Key Figures

Form 144 sale notice: 3,608 shares Aggregate value listed: $191,007.52 Prior sale (Mar 4, 2026): 3,571 shares +2 more

5 metrics

Form 144 sale notice 3,608 shares Form 144 entry dated 06/04/2026

Aggregate value listed $191,007.52 Form 144 entry dated 06/04/2026 for 3,608 shares

Prior sale (Mar 4, 2026) 3,571 shares Sold 03/04/2026 for $187,477.50

Prior sale (Jun 3, 2026) 1,735 shares Sold 06/03/2026 for $92,255.50

Restricted stock vesting 3,608 shares Vesting recorded 06/01/2026 (compensation)

Key Terms

Form 144, Restricted Stock Vesting, Fidelity Brokerage Services LLC

3 terms

Form 144 regulatory

"Form 144 entry dated 06/04/2026 showing 3,608 shares"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Restricted Stock Vesting financial

"06/01/2026 Restricted Stock Vesting listed for 3,608 shares"

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.

Fidelity Brokerage Services LLC other

"Broker listed as Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI"

FAQ

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

What did the LMND Form 144 report show about John S. Peters' holdings?

It reported 3,608 shares vesting on 06/01/2026 and a Form 144 sale notice for those same 3,608 shares valued at $191,007.52 on 06/04/2026.

Has John S. Peters recently sold LMND shares?

Yes. The filing lists sales of 3,571 shares on 03/04/2026 for $187,477.50 and 1,735 shares on 06/03/2026 for $92,255.50.

Through which broker are the LMND shares being transacted?

The Form 144 shows transactions routed through Fidelity Brokerage Services LLC, listed with an aggregate value of $191,007.52 for 3,608 shares on 06/04/2026.

Do the filings state whether the sales were under a trading plan?

The provided excerpt does not state any trading plan or Rule 10b5‑1 instruction; the filing lists the vesting and sale notice but does not include plan disclosures.

What dates are associated with the reported LMND transactions?

Key dates in the excerpt are vesting on 06/01/2026, a Form 144 entry on 06/04/2026, and prior sales on 03/04/2026 and 06/03/2026.

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

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Accepted by SEC EDGAR 06/04/2026 - 11:27 AM 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	3608	191007.52	76820789	06/04/2026	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	06/01/2026	Restricted Stock Vesting	Issuer			3608	06/01/2026	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	03/04/2026	3571	187477.50
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2026	1735	92255.50

144: Remarks and Signature

Remarks
Date of Notice	06/04/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	08/22/2025
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/ Daniel Tucci, 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)