Proposed resale of common shares under Rule 144

LMND submission reports a Rule 144 notice for proposed resale of common stock tied to restricted stock vesting.

Rhea-AI Filing Summary

LMND submission reports a Rule 144 notice for proposed resale of common stock tied to restricted stock vesting. The filing lists a planned sale of 1,735 shares dated 06/01/2026 and prior officer dispositions of 1,773 and 3,571 shares in March 2026.

Insights

Securities Compliance Counsel

Form 144 lists proposed resale under Rule 144 with prior March dispositions noted.

The notice identifies a proposed sale of 1,735 shares tied to Restricted Stock Vesting on 06/01/2026. The filing also records prior dispositions by John S. Peters of 1,773 and 3,571 shares on 03/03/2026 and 03/04/2026.

Timing, settlement mechanics, and whether sales are brokered through Fidelity are listed; cash‑flow treatment to the issuer is not shown in the excerpt. Subsequent broker confirmations or transfer records will determine actual market activity.

Key Figures

Planned resale: 1,735 shares Prior disposition: 1,773 shares Prior disposition: 3,571 shares +1 more

4 metrics

Planned resale 1,735 shares Restricted Stock Vesting on <date>06/01/2026</date>

Prior disposition 1,773 shares Sale on <date>03/03/2026</date> by John S. Peters

Prior disposition 3,571 shares Sale on <date>03/04/2026</date> by John S. Peters

Associated dollar amount (row) $92,255.50 Listed with the 1,735‑share row in the excerpt dated <date>06/03/2026</date>

Key Terms

Restricted Stock Vesting, Rule 144, Fidelity Brokerage Services LLC

3 terms

Restricted Stock Vesting regulatory

"Common | 06/01/2026 | Restricted Stock Vesting"

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.

Rule 144 regulatory

"Form type indicates Rule 144 resale notice and securities to be sold"

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.

Fidelity Brokerage Services LLC market

"Common | Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI"

FAQ

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

What does LMND's Form 144 report?

It reports a proposed resale of common shares under Rule 144. The filing lists a planned sale of 1,735 shares dated 06/01/2026 and prior officer dispositions of 1,773 and 3,571 shares in March 2026.

Who is listed as having sold shares recently in this filing?

John S. Peters is shown as disposing shares in March 2026. The filing records sales of 1,773 shares on 03/03/2026 and 3,571 shares on 03/04/2026, with amounts listed alongside those transactions.

Does the filing state how proceeds will be used?

The excerpt does not specify proceeds use or issuer receipt. It lists per‑transaction dollar amounts adjacent to share counts, but does not state whether proceeds go to the issuer or selling holder.

What broker or broker‑dealer is referenced in the Form 144?

The filing names Fidelity Brokerage Services LLC at the listed address and associates it with the securities to be sold, indicating brokerage involvement in the proposed resale activity.

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

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Accepted by SEC EDGAR 06/03/2026 - 04:52 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	1735	92255.50	76820789	06/03/2026	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	06/01/2026	Restricted Stock Vesting	Issuer			1735	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	03/03/2026	1773	88867.02
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	03/04/2026	3571	187477.50

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	06/03/2026
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/ Gerardo Ibarra-Munoz, 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)