Lemonade (NASDAQ: LMND) Rule 144 sale notice — 3,444 shares listed

Rhea-AI Filing Summary

LMND: A Rule 144 notice lists proposed sales of Common Stock, showing 3,444 shares identified under "Securities To Be Sold" with a 03/01/2025 vesting/compensation origin. The excerpt also records prior dispositions by John S. Peters: 1,735 shares sold on 06/03/2026 for $92,255.50 and 3,608 shares sold on 06/04/2026 for $191,007.52.

Insights

Securities Compliance Analyst

Rule 144 notice lists prospective stock sale and recent insider dispositions.

The filing shows 3,444 shares identified under "Securities To Be Sold" with an origin of "Restricted Stock Vesting" dated 03/01/2025. Rule 144 notices are procedural filings that give brokers and market participants notice of intended resale under resale safe-harbors.

Prior sales by John S. Peters are explicitly recorded: 1,735 shares on 06/03/2026 for $92,255.50 and 3,608 shares on 06/04/2026 for $191,007.52. Subsequent trading activity will depend on broker execution and any holding-period or volume-limitation conditions.

Capital Markets Associate

Notice records a modest resale amount and recent small insider sales.

The listed 3,444 shares tie to restricted stock vesting and are modest in scale relative to typical float sizes. The filing names Fidelity Brokerage Services LLC as a broker/agent in the header.

Cash‑flow treatment and timing for the identified 3,444 shares are not specified in the excerpt; trade execution mechanics and any broker instructions will determine market impact.

Key Figures

Securities to be sold: 3,444 shares Sale by John S. Peters: 1,735 shares Sale by John S. Peters: 3,608 shares +2 more

5 metrics

Securities to be sold 3,444 shares Identified under "Securities To Be Sold" with date 03/01/2025

Sale by John S. Peters 1,735 shares Sold on 06/03/2026 for $92,255.50

Sale by John S. Peters 3,608 shares Sold on 06/04/2026 for $191,007.52

Aggregate recent sales (excerpt) 5,343 shares Sum of 1,735 and 3,608 shares sold on 06/03/2026–06/04/2026

Proceeds recorded $283,263.02 Aggregate of $92,255.50 and $191,007.52 from the two sales

Key Terms

Rule 144, Restricted Stock Vesting, Fidelity Brokerage Services LLC

3 terms

Rule 144 regulatory

"Securities To Be Sold / Securities Sold During The Past 3 Months"

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

"03/01/2025 | 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.

Fidelity Brokerage Services LLC market

"Common | Fidelity Brokerage Services LLC 900 Salem Street"

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Available on EDGAR 07/06/2026 - 11:55 AM Accepted by SEC EDGAR 07/06/2026 - 11:54 AM 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
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

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	3444	272076.00	76820789	07/06/2026	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	03/01/2025	Restricted Stock Vesting	Issuer			3444	03/01/2025	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
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

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does LMND's Form 144 report?

The filing reports a proposed resale of 3,444 shares of Common Stock tied to a 03/01/2025 restricted stock vesting origin, plus recent sales by John S. Peters on 06/03/2026 and 06/04/2026.

Who executed recent LMND insider sales shown?

The excerpt records sales by John S. Peters: 1,735 shares on 06/03/2026 for $92,255.50 and 3,608 shares on 06/04/2026 for $191,007.52.

Are the 3,444 LMND shares already vested?

The filing ties the 3,444 shares to "Restricted Stock Vesting" dated 03/01/2025, indicating the shares originate from a compensation vesting event.

Does the Form 144 say who receives proceeds?

The excerpt does not allocate proceeds; it identifies the broker Fidelity Brokerage Services LLC but does not state the recipient of sale proceeds.

Do recent sales by John S. Peters appear large?

The filing shows two transactions totaling 5,343 shares sold across two dates with aggregate proceeds of $283,263.02; the excerpt does not provide outstanding share counts for scale comparison.