Lemonade (NASDAQ: LMND) files Form 144 to sell 1,220 shares

Rhea-AI Filing Summary

LMND filed a Form 144 reporting an intended sale of 1,220 shares of Common Stock tied to a restricted stock vesting event dated 06/01/2026. The filing also shows a prior sale of 223 shares on 03/03/2026 by Maya Prosor.

Insights

Securities Counsel

Notice under Rule 144 for resale of vested restricted shares.

The filing lists 1,220 shares associated with a restricted stock vesting on 06/01/2026. Rule 144 notices are administrative disclosures of intended resale under resale conditions.

Timing and cash‑flow treatment are not stated in the excerpt; subsequent Form 4 or transaction reports will show completed sales if they occur.

Key Figures

Shares proposed for sale: 1,220 shares Prior sale reported: 223 shares Vesting date: 06/01/2026 +1 more

4 metrics

Shares proposed for sale 1,220 shares Restricted Stock Vesting on <date>06/01/2026</date>

Prior sale reported 223 shares Sold by Maya Prosor on <date>03/03/2026</date>

Vesting date 06/01/2026 Date tied to the 1,220-share vesting event

Filing/cover date shown 06/03/2026 Date shown in the filer information block

Key Terms

Restricted Stock Vesting, Form 144, Securities Sold During The Past 3 Months

3 terms

Restricted Stock Vesting financial

"Securities To Be Sold | 06/01/2026 | Restricted Stock Vesting"

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.

Form 144 regulatory

"Filer Information | 144: Filer Information"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Securities Sold During The Past 3 Months regulatory

"Securities Sold During The Past 3 Months Maya Prosor ... 03/03/2026"

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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	1220	64871.30	76820789	06/03/2026	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	06/01/2026	Restricted Stock Vesting	Issuer			1220	06/01/2026	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	03/03/2026	223	11177.30

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 report?

It reports an intended sale of 1,220 shares tied to a restricted stock vesting on 06/01/2026. The filing notifies the market under resale rules and lists a prior sale of 223 shares on 03/03/2026.

Who previously sold shares according to the filing?

The filing shows Maya Prosor sold 223 shares on 03/03/2026. That prior-sale line is included under "Securities Sold During The Past 3 Months" in the excerpt provided.

Are the shares being sold from compensation or another source?

The 1,220 shares are linked to "Restricted Stock Vesting" with an issuer/compensation designation dated 06/01/2026. The excerpt ties the shares to a vesting compensation event.

Does the Form 144 indicate proceeds or sale timing?

No sale proceeds or execution timing are stated in the excerpt. The filing lists intent to sell under Rule 144; completed sale details would appear in subsequent transaction reports if executed.