Discussion Materials Project William September 27, 2020

Summary of Bid History 2 August 16:Verbal offer of $25 per share Consortium Offers Counter Offers September 9:Counteroffer of $32 with $30-34 collar August 26:Written offer of $25 per share September 3:Verbal offer of $27 per share September 15:Verbal offer of $28.25 per share September 20:Counteroffer of $32 per share with walkaway and hedge structure September 22:Offer of $30 per share with risk share structure to down 20% ($25.76) with walkaway September 24:Counterproposals at $31 – both fixed at 36% walkaway and with hedge at 10% walkaway September 26:Offer of $30 per share with walkaway at book value (down ~29% in BV) August September Consistently included equity rollover option

Summary of Updated Consortium Proposal 3 Price Consideration Arch CFO Francois Morin and Goldman Sachs separately communicated to Jon Levy and Morgan Stanley the consortium’s revised offer on September 26Re-iterated it is their final offer Fixed price of $30.00 per shareRepresents 0.71x P/BV using $42.28 BVPS at 8/30/2020 100% cashRejected rollover option, citing:Limited value for shareholdersOngoing cost of managing small investorsLong private placement processInability to exclude investors / concerns around certain investors coming into the rollover Walkaway Consortium walkaway right if closing book value per share is below $30.00Closing book value defined as:Starting book value per share ($42.28 at 8/30/2020)Plus/Less: Unrealized and realized gains/losses in the non-investment grade portfolio

Stock Price Performance Stock Price Performance since Watford Re ListingStock Price ($), Volume (Shares, MM) Source: Capital IQ, SNL Financial (09/25/2020) Notes:1. Period ending 02/19/2020 4 10/29/2019: All-Time High of $28.90 5/14/2020: All-Time Low of $10.86 $22.02 ~140k sharesPre-COVID Average Daily Volume ~90k sharesPost-COVID Average Daily Volume $25.76Listing-to-COVID VWAP 2/19/2020 (COVID): $24.42 $30.00Offer Price

Source: Capital IQ, SNL Financial (09/25/2020), Company Filings 5 Run-Off Sensitivity Analysis: Existing Contract Through 2025; Sale at 0.80x BV After Peer P/BV Multiples 10% Discount Rate 8% Discount Rate Total Return Reinsurance Traditional Reinsurance Run-Off Analysis and Peer Trading

Select Precedent Final Premium to Initial Offer Squeeze-Outs Insurance Squeeze-Out: Final Premiums / (Discount) to Initial Offer Source: Capital IQ, Company Filings 6 Median: 10.5 Tender Merger Tender Tender Tender Merger Merger Merger Merger Merger Tender Merger Tender Tender $30 Offer Price

Illustration of Proposed Walkaway Mechanic Proposed walkaway at $30 per share / 1.0x P/BV corresponds to:16.3% decline in HPS non-IG portfolio29.0% decline in book value 7 Represents market movement over net assets between 4Q’19 and 1Q’20 (unrealized and realized gains/losses ex. interest income) Condition to close that BVPS is > $30Closing mechanic to provide 3 months from satisfaction of all other precedents to achieve BVPS closing condition Potential Structural Protection

Analysis at Various Prices 8

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