[144] Lemonade, Inc. SEC Filing

Rhea-AI Filing Summary

LMND filed a Form 144 notice for a proposed sale of 5,988 shares of common stock. The filing lists an aggregate market value of $467,064.00, with Fidelity Brokerage Services LLC as broker, an approximate sale date of 11/10/2025, and trading on the NYSE. Shares outstanding were 74,731,027 as of the filing; this is a baseline figure, not the amount being sold.

The filing also reports activity in the prior three months: Adina Eckstein sold 40,000 common shares on 11/07/2025 for gross proceeds of $2,920,868.00. The securities to be sold were acquired via an option granted on 04/05/2022 and paid in cash on 11/10/2025.

Insights

Securities law analyst

Routine Form 144 notice for a modest proposed sale.

Form 144 is a notice of an intended sale by an affiliate or holder of restricted/controlled securities under Rule 144. Here, the filing lists a proposed sale of $467,064.00 in value, representing 5,988 common shares, to be executed on or about 11/10/2025 on the NYSE via Fidelity Brokerage Services LLC. This is an administrative disclosure, not a completed transaction.

The excerpt also notes a prior three‑month sale: Adina Eckstein sold 40,000 shares on 11/07/2025 for gross proceeds of $2,920,868.00. Shares outstanding are shown as 74,731,027; this is a baseline figure. Overall, the disclosure permits sales under Rule 144; actual impact depends on execution details.

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	5988	467064.00	74731027	11/10/2025	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	11/10/2025	Option Granted - 04/05/2022	Issuer			5988	11/10/2025	Cash

* 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
Adina Eckstein 5 Crosby Street 3rd Floor New York NY 10013	Common	11/07/2025	40000	2920868.00

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 LMND’s Form 144 disclose?

It discloses a proposed sale of 5,988 shares of common stock with an aggregate market value of $467,064.00.

When is the proposed sale of LMND shares expected?

The approximate date of sale is 11/10/2025.

Which broker and exchange are listed for the LMND sale?

Broker: Fidelity Brokerage Services LLC; Exchange: NYSE.

How many LMND shares were outstanding as referenced?

Shares outstanding were 74,731,027.

Were there LMND shares sold in the past three months?

Yes. Adina Eckstein sold 40,000 shares on 11/07/2025 for gross proceeds of $2,920,868.00.

How were the securities to be sold acquired?

They were acquired via an option granted on 04/05/2022 and paid in cash on 11/10/2025.