Lemonade insider files Form 144 to sell 2,718 restricted shares on NYSE

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) filing a Form 144 reports proposed sale of restricted common stock by an insider. The notice states 2,718 shares held at Fidelity Brokerage will be offered with an aggregate market value of $136,830.37, and an approximate sale date of 09/03/2025 on the NYSE. The shares were acquired by restricted stock vesting on 08/29/2025 and received as compensation. The filing lists prior sales by the same person within three months: 1,494 shares (06/03/2025), 6,543 shares (06/23/2025), and 38,155 shares (08/13/2025) with gross proceeds shown.

Positive

• Compliance disclosure completed: Form 144 provides required details (shares, broker, acquisition date, sale date, aggregate value).
• Source of shares identified: Securities were acquired via restricted stock vesting and classified as compensation.

Negative

• Significant insider sales in past three months: Aggregated recent disposals total 46,192 shares, which may attract investor attention.
• Potential dilution/liquidity pressure: Large insider disposals could increase supply if executed into market, based on reported prior gross proceeds.

Insights

Financial Analyst

TL;DR: Insider intends to sell recently vested compensation shares totaling 2,718, following multiple significant sales earlier in the quarter.

The filing documents a proposed sale of 2,718 vested restricted shares valued at $136,830.37. Prior three-month dispositions by the same individual total 46,192 shares with reported gross proceeds, indicating active insider liquidity. For investors, repeated insider sales can signal personal portfolio rebalancing rather than company fundamentals; the filing provides no nonpublic operational information. Impact depends on relative size versus public float and market reaction to insider activity.

Corporate Governance Expert

TL;DR: The notice is a routine compliance disclosure for Rule 144 sales of vested restricted stock by an insider.

The Form 144 appears procedurally complete: it identifies the class, broker, number of shares, aggregate value, acquisition date (08/29/2025) and payment type (compensation). It also lists recent sales by the same person, which is relevant for aggregated sale calculations under Rule 144. The signer represents no undisclosed material information. No allegations, restrictions, or plan adoption dates are included in the text.

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	2718	136830.37	73886417	09/03/2025	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	08/29/2025	Restricted Stock Vesting	Issuer			2718	08/29/2025	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	06/03/2025	1494	52664.98
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/23/2025	6543	294435.00
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	08/13/2025	38155	2289300.00

144: Remarks and Signature

Remarks

Date of Notice

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 the LMND Form 144 disclose?

The filing discloses a proposed sale of 2,718 common shares valued at $136,830.37, to be sold on the NYSE on or about 09/03/2025.

How were the shares acquired that are being sold under the LMND Form 144?

The shares were acquired on 08/29/2025 through restricted stock vesting and were received as compensation.

Have there been recent sales by the same person filing this LMND Form 144?

Yes. The filing lists sales in the past three months of 1,494, 6,543, and 38,155 shares on 06/03/2025, 06/23/2025, and 08/13/2025, respectively.

Which broker is handling the proposed LMND sale?

The broker listed is Fidelity Brokerage Services LLC, located at 900 Salem Street, Smithfield RI 02917.

Does the Form 144 assert any undisclosed material information?

By signing, the person represents they do not know of any material adverse information about the issuer that has not been publicly disclosed.