[Form 4] Enstar Group Insider Trading Activity

Rhea-AI Filing Summary

Lemonade, Inc. (symbol LMND) has filed a Form 144 notice covering a proposed sale of 11,000 common shares. The shares are intended to be sold on 07 July 2025 through Fidelity Brokerage Services LLC on the NYSE at an aggregate market value of $466,400. The notice states that 73,266,170 shares of the class are outstanding, so the planned sale represents roughly 0.015 % of that total.

The filing is submitted on behalf of Timothy E. Bixby, the “person for whose account the securities are to be sold.” Acquisition information shows the shares derive from an option granted 01 Dec 2019, exercised for cash on 07 July 2025.

Prior insider activity: Over the past three months, the same seller has executed seven separate transactions totaling 45,916 shares for gross proceeds of approximately $1.86 million, with individual sale dates ranging from 03 June 2025 to 30 June 2025.

The signatory affirms awareness of Rule 10b5-1 obligations and declares no undisclosed material adverse information. No additional financial or operational data about Lemonade is included in this Form 144.

Positive

• Sale represents only 0.015 % of outstanding shares, implying negligible dilution or liquidity impact.
• Full Rule 144 disclosure including prior 90-day transactions and broker details, indicating regulatory compliance and transparency.

Negative

• Continued insider selling trend: 45,916 shares already sold over past three months plus an additional planned 11,000 shares.
• Gross proceeds of ~$1.86 M in recent sales may be interpreted by some investors as reduced insider confidence.

Insights

Financial Analyst

TL;DR: Modest–scale insider sale adds to recent $1.9 M disposals; unlikely to affect float but continues selling trend.

This Form 144 indicates another 11 k-share sale by Timothy E. Bixby, bringing his three-month total to roughly 46 k shares worth $1.86 M. The planned sale equals only 0.015 % of shares outstanding, so share-supply impact is minimal. Nevertheless, the continued liquidation pattern may be viewed cautiously by investors who monitor insider sentiment, especially because the sales are clustered within a single quarter. Absent any accompanying business update, the filing is information-only; valuation impact should therefore be limited unless the market extrapolates a negative signal from the selling cadence.

Corporate Governance Specialist

TL;DR: Routine Rule 144 filing; demonstrates compliance but flags sustained insider selling streak.

From a governance standpoint, the issuer is meeting disclosure requirements: the form details broker, dates, share counts, prior 90-day sales, and asserts no undisclosed MNPI. The proposed transaction appears to follow a structured plan (possible 10b5-1 usage noted), supporting transparency. However, consecutive sales totalling nearly $2 M within three months can raise perception risk among shareholders tracking leadership alignment. Because the stake sold is minute relative to float, I classify the market impact as low but directionally negative.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

X

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Oros Anne

(Last) (First) (Middle)

C/O J.C. FLOWERS & CO. LLC

1301 AVENUE OF THE AMERICAS, 16TH FLOOR

(Street)

NEW YORK NY 10019

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Enstar Group LTD [ ESGR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
	Officer (give title below)	X	Other (specify below)
			See Remarks

3. Date of Earliest Transaction (Month/Day/Year)
07/02/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Ordinary Shares	07/02/2025		J(1)		33,358	D	(1)	0	I	See footnote(2)

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. On July 2, 2025, pursuant to a rollover and support agreement by and among Elk Topco, LLC ("Topco"), the John. J. Oros 1998 Family Trust (the "Oros Trust") and J.C. Flowers & Co. LLC, and that certain Agreement and Plan of Merger by and among, the Issuer, Deer Ltd., Deer Merger Sub Ltd., Elk Bidco Limited and Elk Merger Sub Limited, the Oros Trust transferred, contributed and delivered to Topco all Ordinary Shares held by the Oros Trust in exchange for equity interests therein.

2. The reported securities were directly held by the Oros Trust. Anne Oros, in her capacity as trustee of the Oros Trust, may have been deemed to beneficially own the reported securities. Anne Oros disclaims beneficial ownership of the securities held directly by the Oros Trust except to the extent of her pecuniary interest therein, and this report shall not be deemed an admission that Anne Oros was the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

Remarks:

The Reporting Person was a member of a "group" for purposes of Section 13(d) of the Securities Exchange Act of 1934 (the "Group") that beneficially owned more than 10% of the Issuer's outstanding Ordinary Shares. The other members of the Group include Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC, TSS Sub-Fund Holdco, LLC, Alan Waxman, J. Christopher Flowers, Paula Mims (not in her individual capacity but solely as executor of the Estate of Nimrod T. Frazer), Frazer Holdings LLC, the Estate of Nimrod T. Frazer, the Hyman 2018 Family Trust, Stuart Schlesinger, David G. Walsh, Steven D. Arnold, the Arnold 1997 Limited Partnership and SAS GP, L.L.C. (collectively, the "Other Group Members"). The Reporting Person disclaims beneficial ownership of the Ordinary Shares of the Issuer beneficially owned by the Other Group Members except to the extent of the Reporting Person's pecuniary interest therein.

	/s/ Anne Oros	07/07/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

How many Lemonade (LMND) shares are being proposed for sale in the latest Form 144?

The filing covers 11,000 common shares with an estimated market value of $466,400.

What percentage of LMND’s outstanding shares does the 11,000-share sale represent?

Approximately 0.015 % of the 73,266,170 shares outstanding.

Who is the selling shareholder listed in the Form 144 for Lemonade?

The notice is filed for Timothy E. Bixby, as the person for whose account the shares will be sold.

How many LMND shares has Timothy E. Bixby sold in the last three months?

He has already sold 45,916 shares across seven transactions, generating roughly $1.86 million in gross proceeds.

When is the proposed sale date for the 11,000 LMND shares?

The approximate sale date disclosed is 07 July 2025.