[144] Lemonade, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 notice for Lemonade, Inc. (LMND): The filer reports a proposed sale of 282 common shares through Fidelity Brokerage Services with an aggregate market value of $14,196.53. The shares were acquired via restricted stock vesting on 08/29/2025 and payment was recorded as compensation on the same date. The approximate sale date is listed as 09/03/2025 and the securities trade on the NYSE. The filing shows 73,886,417 shares outstanding. The filer also disclosed a prior sale on 06/03/2025 of 252 shares for $8,883.25. The notice includes the required representation that the seller is not aware of undisclosed material adverse information.

Positive

• Transparent disclosure of the proposed sale including broker, acquisition date, nature (restricted stock vesting), and aggregate market value
• Includes prior sale in the past three months (252 shares on 06/03/2025), supporting completeness of insider sale history
• Seller certification that they are not aware of undisclosed material adverse information, as required

Negative

• None.

Insights

Securities Compliance Analyst

TL;DR: Routine Rule 144 disclosure showing an insider sale of vested restricted stock; documentation aligns with Rule 144 requirements.

The filing documents a proposed sale of 282 vested shares via a broker with acquisition and payment dated 08/29/2025 and an approximate sale date of 09/03/2025. The notice includes prior sales in the past three months, satisfying the look-back transparency. From a compliance perspective this Form 144 contains the core elements: acquisition date, nature (restricted stock vesting), broker details, proposed sale amount and value, and the seller's representation regarding material non-public information. No material omissions are apparent within the content provided.

Corporate Governance Specialist

TL;DR: Disclosure is standard for insider liquidity of vested awards and provides clear broker and transaction details.

This Form 144 shows an individual selling shares that vested as compensation. It lists the broker, number of shares, aggregate market value, outstanding shares, and a recent prior sale. For governance review, the filing documents the mechanics of insider disposition and reiterates the seller's certification about undisclosed material information. The size of the transaction relative to total outstanding shares is provided, enabling assessment of potential governance or signaling impact.

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	282	14196.53	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			282	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
Maya Prosor 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2025	252	8883.25

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 Form 144 for Lemonade (LMND) disclose?

It discloses a proposed sale of 282 common shares acquired via restricted stock vesting on 08/29/2025, to be sold approximately on 09/03/2025 through Fidelity.

How much is the aggregate market value of the shares proposed to be sold?

The aggregate market value is reported as $14,196.53 for the 282 shares.

Did the filer sell shares recently before this filing?

Yes. The filing reports a prior sale on 06/03/2025 of 252 shares for $8,883.25.

What was the nature and payment for the acquired shares?

The shares were acquired via restricted stock vesting and the payment nature is listed as compensation on 08/29/2025.

On which exchange are the securities listed?

The securities are listed on the NYSE as indicated in the filing.