Board of Directors Follow-Up Project William August 19, 2020

Section 1 Evaluation of Arthur Proposal 2

Terms Comments Price $25.00 per share$500MM equity value(1) Proposal represents:P/BV of 0.64xDiscount to initial investment of $40.00(2)13% discount to all-time high of $28.905% premium to $23.78 VWAP since direct listingPremium of 49% to current price(3) Consideration All cash Crystalizes loss for initial shareholdersNo opportunity to participate in upsideEither as part of private investment in “new” Watford or as shareholder in ArthurProvides certainty on valueFull liquidity Structure Arthur and two private equity partners to acquire William Unusual to negotiate sale with three partiesCreates risk regarding transaction certaintyNeed to better understand terms among parties and conditionalityNeed to understand constraints imposed by tax requirements Partner Approvals Approved by Arthur board and investment committees at two private equity firms As a practical matter, have only approved basic termsWill ultimately need approval for definitive agreements, when / if reached Initial Assessment of Arthur Verbal Indication Evaluation of Arthur Proposal 3 Notes:Based on 20.0MM diluted shares outstanding as of 2Q’20Reflects price per share in March 2014 offeringBased on August 14, 2020 close price of $16.74/share

Comments Timing Can complete transaction in 2-3 weeksCited motivation to complete quickly given importance of January 1 renewalsOther drivers of timing unclear Diligence Not addressed in initial discussionArthur has had ongoing access to data roomShould confirm no material items outstandingWhere are partners in their diligence process? Funding Ability for Arthur to finance / guarantee completion?Sources / uses detail not provided Third Party Approvals What approvals are necessary and who bears risk? Service Agreements Arthur indicated potential room to move if have greater certainty around Henry contract and ability to lower allocationEconomics of Henry and Arthur agreements critical to overall value Initial Assessment of Arthur Verbal Indication Evaluation of Arthur Proposal 4

Preliminary Illustrative Responses to Arthur Evaluation of Arthur Proposal 5 Valuation 1 $25 price not sufficiently compelling Offer of $25 per share represents:0.64x BVPS13% discount to all-time high of $28.90Substantial discount to sector multiplesRun-off transaction multiples of 0.40x-0.89x P/BV, implying $15.53 - $34.55Bermuda reinsurance transaction multiples of 0.52x -1.26x P/BV, implying $20.19 - $48.91Company has alternatives to drive higher values than this proposalOngoing scrutiny and pressure from activist investor Form of Offer Must be provided in writing to properly evaluateNeed substantially more detail around key items, including:StructureFundingDiligenceConditionality Consideration / Structure 2 Ability for Arthur to sign / close transaction without equity commitment from PE firmsAbility for shareholders to participate in upside would be attractive Execution / Terms Merger vs. tender offerMajority of minority requirementAbility to improve price if reach favorable outcome with Henry 4 3

Section 2 Sensitivity Analyses 6

Hybrid Scenario Dividend Discount Model Summary Projections based on partial combination of scenarios presented in prior presentation as directed by managementAssumes 2 point reduction in fees to AUL: $13.5MM savings expected in 2021Adjustments to Henry assets: $9.4MM savings expected in 2021Assumes 35bp reduction to investment management expenseTransfer $500MM from Henry to investment grade strategyNo sidecarDiscount rate of 10.0% based on Watford’s cost of equityExit multiple of 0.45x BVPS based on Watford’s current trading multiple(1) Notes:As of 08/11/2020Includes loss reserve equity, senior notes, contingent redeemable preferred shares less intangible assets Sensitivity Analyses 7 (2)

Combined Ratio Sensitivity Analysis Base Case vs. Hybrid Scenario Base Case:Assumed baseline combined ratio and management feesNo de-risking of portfolioNo sidecarHybrid Scenario:Assumed 2 point reduction in fees to AUL and 35bp reduction to investment management expenseTransfer $500MM from Henry to investment grade strategyNo sidecarDiscount rate of 10.0% based on Watford’s cost of equity Sensitivity Analyses 8 Base Case Hybrid Scenario

Run-Off Reserve Sensitivity Outcome 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 reservesPresent discounted value of Arch run-off fees over 5 years: $39.5 - $46.3MM or $1.98 - $2.31/share Sensitivity Analyses 9 Run-Off Reserve Development

Appendix Supporting Materials 10

Peer Trading Comparables Source: Company Filings, Capital IQ, SNL Financial (08/11/2020)Notes:Reflects median annual combined ratio over the last 10 fiscal years, or since inception as appropriateReflects standard deviation of annual combined ratios over the last 10 fiscal years, or since inception as appropriate Reflects median annual BVPS growth, including dividends, over the last 10 fiscal years, or since inception as appropriateReflects standard deviation of annual BVPS growth, including dividends, over the last 10 fiscal years, or since inception as appropriate Supporting Materials 11 (1) (2) (3) (4)

Select Precedent Transactions (1 of 2) Run-Off P&C Transactions Limited publicly available data on P&C run-off transactionsOn a recent P&C run-off transaction Morgan Stanley worked on, bids were generally in the 0.85-1.00x range of tangible book valueGreenlight Re rumored to have rejected run-off bid at around ~0.9x P/BV in late 2019 12 Select Precedent Transactions Source: Capital IQ, SNL Financial, Company Filings and MaterialsNotes:Deal value reflects implied value of 100% stake; book value and tangible book value reflect 12/31/2019 figures (nearest available) (1) (1) (1)

Select Precedent Transactions (2 of 2) 13 Select Precedent Transactions Supporting Materials Source: Capital IQ, SNL Financial, Company Filings and MaterialsNotes:Represents premium paid to public shareholders; does not incorporate value to CMIHBook 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 AXISUtilizes 2018E EPS (instead of NTM EPS) as NTM artificially low due to 4Q’17 losses (3) (3) (2) (2) (1) (4)

Top 20 Current Active Institutional Investors (1) 14 Top 20 Institutional Holders by Investment Style (1) WTRE Ownership Momentum Institutional Ownership As of 2Q’20 Source: Thomson Notes:As of 2Q'2020; excludes index funds and broker-dealers Increase in ownership by ≥ 5% Decrease in ownership by ≥ 5% Supporting Materials

15 Cost of Equity Analysis Watford Cost of Equity Analysis Supporting Materials Source: Capital IQ, SNL Financial (08/11/2020)

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