Investor Presentaiton

BOOK VALUE PER SHARE June 30, 2021 December 31, 2020 Numerator: Total Enstar shareholders' equity Less: Series D and E preferred shares Total Enstar ordinary shareholders' equity (A) Proceeds from assumed conversion of warrants (1) $7,187,308 510,000 6,677,308 $6,674,395 510,000 6,164,395 20,229 Numerator for fully diluted book value per ordinary share calculations (B) $6,677,308 $6,184,624 July Share Repurchases (2) (890,023) Numerator for pro forma fully diluted book value per ordinary share calculations (C) 5,787,285 Denominator: Ordinary shares outstanding (D) (3) 21,604,803 21,519,602 Effect of dilutive securities: Share-based compensation plans (4) Warrants (1) Fully diluted ordinary shares outstanding (E) July Share Repurchases (2) Pro forma fully diluted ordinary shares outstanding (F) Book value per ordinary share: 317,380 298,095 21,922,183 175,901 21,993,598 Basic book value per ordinary share = (A)/(D) Fully diluted book value per ordinary share = (B)/(E) (3,794,711) 18,127,472 $309.07 $304.59 $319.25 $286.45 $281.20 Pro forma fully diluted book value per ordinary share = (C) / (F) (1) Warrants to acquire 175,901 Series C Non-Voting Ordinary Shares for an exercise price of $115.00 per share were exercised on a non-cash basis during the six months ended June 30, 2021, which resulted in a total of 89,590 Series C Non-Voting Ordinary Shares being issued in the period. (2) Represents shares repurchased in transactions described within the explanatory notes below. (3) Ordinary shares outstanding includes voting and non-voting shares but excludes ordinary shares held in the Enstar Group Limited Employee Benefit Trust (the "EB Trust") in respect of awards made under our Joint Share Ownership Plan, a sub-plan to our Amended and Restated 2016 Equity Incentive Plan (the "JSOP"). (4) Share-based dilutive securities include restricted shares, restricted share units, and performance share units ("PSUs"). The amounts for PSUs, and for ordinary shares held in the EB Trust in respect of the JSOP, are adjusted at the end of each period end to reflect the latest estimated performance multipliers for the respective awards. The JSOP shares did not have a dilutive effect as at June 30, 2021. Pro Forma Fully Diluted Book Value Per Ordinary Share - Non-GAAP In addition to presenting fully diluted book value per ordinary share calculated as of June 30, 2021, we have presented pro forma fully diluted book value per share, which reflects adjustments to fully diluted book value per share as of June 30, 2021 to give effect to share repurchases that were completed subsequent to June 30, 2021. On July 22, 2021, we completed a repurchase of 3,749,400 of our ordinary shares held by funds managed by Hillhouse Group for a price of $234.52 per share, totaling $879.3 million in aggregate. The shares represented these funds' entire interest in Enstar, which constituted 16.9% of total ordinary shares and 9.4% of voting ordinary shares. Subsequent to June 30, 2021, we have also repurchased 45,311 shares for $10.7 million as part of our ordinary share Repurchase Program before terminating the Repurchase Program on July 15, 2021. We believe that the presentation of pro forma fully diluted book value per share to give effect to these transactions provides readers of our financial statements with useful information regarding the impact of this significant strategic share repurchase that had a material impact on the number of our outstanding ordinary shares. We do not expect to present this measure in future periods. Pro forma fully diluted book value per share is calculated by adjusting the numerator and denominator of fully diluted book value per share to give effect to the completed share repurchase transactions described above. ENSTAR Property of Enstar Group Limited - Not for Distribution 20

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