Board of Directors Follow-Up Project William September 4, 2020

Summary of Revised Verbal Offer and Key Points Raised Subsequent to receiving Watford’s letter and feedback from Morgan Stanley, Goldman Sachs met with the consortium, including Arch’s board of directors 2 Revised Offer Alternatives Investment Portfolio Business Plan / Ratings Provided revised verbal offer of $27 per share in cashNoted it represents an 8% improvement vs. original $25 offer60% premium to current, represents 0.69x P/BV at 6/30/2020Decided to provide improved, non-public offer in hopes of completing transactionSuggested private equity investors argued to make $25 offer public Challenged Watford’s practical ability to pursue alternativesDid not raise run-off Investment portfolio raised as a key source of concernAcknowledged improvement in value since March, but see potential for further volatilityChallenged value attributed to post-6/30 book value improvement, as would want to diligence the marks and understand risks Believe business plan is highly uncertain if company’s ratings remain on watch or are downgradedCounterparties may be wary of placing of business or demand collateralNoted that if this transaction is not successful, may pursue sidecar strategy, which could constrain the amount of business offered to Watford beyond the requirements of the service agreement Rollover Reiterated prior rejection of ability of current Watford holders to participate / roll Arch Relationship Took umbrage regarding reference to fees paid to Arch as believe were for services renderedHowever, did not attempt to dispute high combined ratio

Watford Re Stock Price Analysis Stock Price Performance since Watford Re ListingStock Price ($), Volume (Shares, MM) Source: Capital IQ, SNL Financial (09/03/2020) Notes:1. Period ending 02/19/2020 3 10/29/2019: All-Time High of $28.90 5/14/2020: All-Time Low of $10.86 $16.87 ~140k sharesPre-COVID Average Daily Volume ~70k sharesPost-COVID Average Daily Volume $25.76Listing-to-COVID VWAP 2/19/2020 (COVID): $24.42

Watford Re Trading Multiple Performance Source: Capital IQ, SNL Financial (09/03/2020) Notes:Traditional (Re)insurance Peers include ACGL, AXS, RE, RNR and Y 4 01/01/2015 – 09/03/2020 (x) Price / Book Value (1) 0.43x 0.62x 0.60x 0.94x

Precedent Reinsurance Transactions Source: Capital IQ, SNL Financial, Company Filings and MaterialsNotes:Book value and tangible book value reflect 2Q20 figures as referenced in Third Point investor presentation, which preceded Sirius earnings announcementPartnerRe 6/30/2015 book value adjusted for $315MM breakup fee payable to AXIS 5 (1) (2) (1) (2)

Standalone Alternatives: Sensitivity Analysis Base Case vs. De-Risked Investment Portfolio Scenario 6 De-Risk Investment Portfolio Description Transfer $500MM from HPS to investment grade strategy Baseline assumptions includingHardening marketAchievement of 10%+ ROE at 99% combined ratio Base Case Sensitivity:Cost of Equity / Terminal Multiple Sensitivity:Combined Ratio / Terminal Multiple Does not include investment gains of $3.17/share from June 30 to August 12

Run-Off Analysis: Sensitivities Projections based on Company Run-Off ModelAssumes business is sold after 5 years of run-offAssumes 100% asset reallocation to investment grade assets upon run-offOutcome of run-off scenario dependent on existing reserves and the actual payout of lossesTo assess impact of adverse or favorable development, showing a range of +/- 10% reserve chargeAssumes reserve charge is taken in Q3 2020 and run-off with existing reserves 7 Run-Off Reserve Development Sensitivity Cost of Equity Sensitivity Does not include investment gains of $3.17/share from June 30 to August 12

Appendix Supporting Materials 8

Base Case - Dividend Discount Model Summary Discount rate of 10% based on Watford’s cost of equityExit multiple of 0.43x BVPS based on Watford’s current trading multiple(1) Notes:As of 09/03/2020Includes loss reserve equity, senior notes, contingent redeemable preferred shares less intangible assets Supporting Materials 9 (2) Does not include investment gains of $3.17/share from June 30 to August 12

Run-Off Analysis - Dividend Discount Model Summary Discount rate of 10% based on Watford’s cost of equityExit multiple of 0.80x BVPS based on precedent run-off dealsPresent discounted value of Arch run-off fees over 5 years: $43.5MM or $2.17/share Notes:Based on 50% of net reserves Supporting Materials 10 (1) Does not include investment gains of $3.17/share from June 30 to August 12

11 Cost of Equity Analysis Watford Cost of Equity Analysis Supporting Materials Source: Capital IQ, SNL Financial (09/03/2020)

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