Investor Presentaiton

KEY MILESTONES Executing market-leading solutions to the global (re)insurance market for 27+ years Joint venture with private equity investors created Castlewood Commenced first four Lloyd's RITC transactions through Holdings Limited Became Acquired StarStone "Enstar Shelbourne Group Syndicate 2008 Entered Limited" active underwriting Began trading on NASDAQ Completed reinsurance transaction with QBE and RSA Completed 4 RITC transactions with Am Trust Acquired BorgWarner Morse TEC business; acquired Atrium Completed reinsurance transaction with Coca-Cola Launched Kayla Re with Hillhouse & Stone Point Launched Enhanzed Re with Allianz & Hillhouse Acquired Kayla Re Acquired Maiden Re North America Completed recapitalization of StarStone U.S. Completed first IBT transaction in the US Completed a novation agreement with Lyft Completed reinsurance transaction with Hannover Re, Munich Re, AXA XL and Aspen Completed reinsurance transactions with Coca- Cola, Liberty Mutual, CNA, AXA XL, Hiscox and ProSight Announced reinsurance transaction with RSA 1993 2001 2007 2008 2013 2014 2016 2017 2018 2019 2020 2021 Founded in Bermuda by members of current management team 2001-2010 40 acquisitive transactions ENSTAR 2011-2020 63 acquisitive transactions 100+ acquisitive transactions to date Property of Enstar Group Limited - Not for Distribution 5

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