Enstar : Presentation Slides for 2021 Mid-Year Update

ENSTAR GROUP LIMITED

Company Overview

Mid-Year Update

August 2021

enstargroup.com

DISCLAIMER

For more complete information about Enstar Group Limited, you should read our reports filed with the SEC. You may get these documents for free through EDGAR

on the SEC website at www.sec.gov, or through our website at https://investor.enstargroup.com/sec-filings.

IMPORTANT INFORMATION REGARDING FORWARD-LOOKING STATEMENTS

This presentation, and oral statements made with respect to information contained in this presentation, may include certain forward-looking statements regarding our views with respect to our business, operations, loss reserves, strategy, investment portfolio, economic model, and our expected performance for future periods, as well as the insurance market and industry conditions. These statements are intended as "forward-looking statements" under the Private Securities Litigation Reform Act of 1995. Actual results may materially differ from those set forth in the forward-looking statements. You may identify forward- looking statements by the use of words such as "believe," "expect," "plan," "intend," "anticipate," "estimate," "predict," "potential," "may," "should," "could," "will" or other words or expressions of similar meaning, although not all forward-looking statements contain such terms.

Forward-looking statements involve significant risks and uncertainties, including risks of changing and uncertain economic conditions, the success of implementing our business strategies, the adequacy of our loss reserves, ongoing and future regulatory developments disrupting our business, lengthy and unpredictable litigation, risks relating to our acquisitions, increasing competitive pressures, loss of key personnel, risks relating to our active underwriting businesses, the performance of our investment portfolio and liquidity, and other factors detailed in our Annual Report on Form 10-K for the year ended December 31, 2020, our Form 10-Q for the interim period ended June 30, 2021, and our other reports

filed from time to time with the Securities and Exchange Commission ("SEC").

Any forward-looking statement you see or hear during the presentation reflects Enstar Group Limited's current views with respect to future events and is subject to these and other risks, uncertainties and assumptions. If any of these risks or uncertainties materialize, or if our underlying assumptions prove to be incorrect, actual results may vary significantly from what we projected. You are cautioned not to place undue reliance on these forward- looking statements, which speak only as of the date on which they are made. The date of this presentation is listed on the cover page and Enstar does not undertake to update or keep it accurate after such date.

ADDITIONAL INFORMATION

The company has an effective shelf registration statement (including a prospectus) on file with the SEC. Any offering of securities will be made only by means of a prospectus supplement, which will be filed with the SEC. In the event that the company undertakes an offering, you may obtain a copy of the prospectus supplement and accompanying prospectus for the offering by visiting EDGAR on the SEC website at www.sec.gov.

Property of Enstar Group Limited - Not for Distribution

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A LEADING GLOBAL

INSURANCE GROUP

Enstar is a leading global insurance group that offers innovative capital release solutions through our network of group

companies. We have a 27+ year history of operating in the run-offspace, with more than 100 total acquisitive transactions completed to date.

OUR HISTORY

Enstar Group has become a global leader in releasing value for the world's largest insurers and reinsurers

1993	2001	2007
Founded by				Merged with
			Enstar to form
members of
			Enstar Group
the current		Holding
		Limited
management		company
		(ticker:ESGR)
team in		formed
Bermuda in				Public listing
1993
			Nasdaq
CASTLEWOOD		CASTLEWOOD		ENSTAR

2020

$8.7bn total capital under management

1

ENSTAR

1 Total Capital under management includes includes, Ordinary Equity, Preferred Shares, Redeemable Non- controlling Interest and non- controlling Interest, Public Debt and Bank Debt

Property of Enstar Group Limited - Not for Distribution

4

KEY MILESTONES

Executing market-leading solutions to the global (re)insurance market for 27+ years

Joint venture

Completed

Completed

4 RITC

with private

recapitalization of

transactions

equity investors

StarStone U.S.

Completed

Completed

with

created

Commenced first

AmTrust

Completed first

reinsurance

Castlewood

reinsurance

IBT transaction in

transactions

Holdings

four Lloyd's RITC

Acquired

transaction with

Acquired

with Coca-

the US

Limited

Became

transactions

QBE and RSA

BorgWarner

Cola, Liberty

through

StarStone

Morse TEC

"Enstar

Shelbourne

Completed a

Mutual, CNA,

Group

Syndicate 2008

Entered

Launched

novation

AXA XL,

Limited"

active

Completed

agreement

Hiscox and

EnhanzedRe with

underwriting

reinsurance

with Lyft

ProSight

Began trading

Allianz & Hillhouse

business;

transaction with

Completed

Announced

on NASDAQ

acquired

Coca-Cola

Acquired

reinsurance

reinsurance

Atrium

KaylaRe

transaction with

transaction with

Launched

Acquired Maiden

Hannover Re,

RSA

KaylaRe with

Re North

Munich Re, AXA

Hillhouse & Stone

America

XL and Aspen

Point

1993

2001

2007

2008

2013

2014

2016

2017

2018

2019

2020

2021

Founded in	2001-2010	2011-2020	100+
Bermuda by	40	63
acquisitive
members
acquisitive	acquisitive	transactions
of current
transactions	transactions	to date
management
team

Property of Enstar Group Limited - Not for Distribution

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