Lemonade (NYSE: LMND) insider plans Rule 144 sale after stock vesting

Rhea-AI Filing Summary

Lemonade insider plans additional stock sale under Rule 144. A holder of Lemonade common stock filed a notice to sell 3,554 shares through Fidelity Brokerage Services on the NYSE, with an aggregate market value of $287,874 and 74,731,027 common shares outstanding. The shares to be sold were acquired on 12/01/2024 via restricted stock vesting as compensation from the issuer. The same seller has already completed multiple common stock sales over the prior three months, including 18,930 shares on 11/20/2025 for gross proceeds of $1,377,536.10.

Insights

Equity Capital Markets Analyst

Routine Lemonade insider sales under Rule 144 with limited size.

An insider in Lemonade (LMND) has filed a Rule 144 notice to sell 3,554 common shares through Fidelity on the NYSE, tied to restricted stock that vested on 12/01/2024 as compensation. The filing also lists 74,731,027 common shares outstanding, which makes this planned sale small relative to the company’s total equity.

The same seller reported several prior sales over the last three months, such as 18,930 shares on 11/20/2025 for gross proceeds of $1,377,536.10. These transactions illustrate ongoing liquidity events from equity awards rather than a large block disposal. The seller also represents that they are not aware of undisclosed material adverse information, aligning the transactions with Rule 144 and 10b5-1 requirements.

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	3554	287874.00	74731027	12/10/2025	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	12/01/2024	Restricted Stock Vesting	Issuer			3554	12/01/2024	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	11/20/2025	18930	1377536.10
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	11/24/2025	3798	278205.02
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	12/02/2025	2677	194711.06
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	12/03/2025	2667	193010.79

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 filing for Lemonade (LMND) disclose?

It discloses that an insider plans to sell 3,554 Lemonade common shares on the NYSE under Rule 144, with an aggregate market value of $287,874.

How many Lemonade (LMND) shares are outstanding in this filing?

The filing reports that 74,731,027 common shares of Lemonade are outstanding.

How did the insider acquire the Lemonade (LMND) shares being sold?

The 3,554 shares to be sold were acquired on 12/01/2024 through restricted stock vesting as compensation from the issuer.

Which broker is handling the proposed Lemonade (LMND) insider sale?

The filing lists Fidelity Brokerage Services LLC, based in Smithfield, Rhode Island, as the broker for the planned NYSE sale.

What prior Lemonade (LMND) stock sales by this insider are reported?

Over the past three months, the insider reported several common stock sales, including 18,930 shares on 11/20/2025 for $1,377,536.10 in gross proceeds.

Does the Lemonade (LMND) insider state anything about undisclosed information?

By signing the notice, the seller represents that they do not know any material adverse information about Lemonade’s operations that has not been publicly disclosed.