First Quarter 2023 June 2023

ProAssurance Investor Briefing | June 2023 3 Mission, Vision, & Values The ProAssurance Mission We Protect Others. Corporate Values Integrity | Leadership | Relationships | Enthusiasm Our Brand Promise We will honor these values in the execution of treated fairly to perform our mission and realize our vision.

ProAssurance Investor Briefing | June 2023 4 At a Glance All employee and financial data as of 3/31/23. Business Unit Principal Offices Employees Lines of Business HCPL 8 607 Healthcare professional liability Medmarc 1 35 Medical technology liability Small Business Unit 1 100 Podiatrists, chiropractors, dentists, and lawyers Eastern 7 251 Workers’ Compensation & captive facilities (all lines) PRA Corporate 1 93 Corporate functions • Healthcare-centric specialty insurance writer ◦ Specialty Property & Casualty ▪ Healthcare Professional Liability (HCPL) ▪ Life Sciences and Medical Technology Liability ▪ Small Business Unit ◦ Workers' Compensation Insurance ◦ Segregated Portfolio Cell (SPC) Reinsurance ◦ Lloyd's of London Syndicates • Total Assets: $5.7 billion • Shareholders' Equity: $1.1 billion • Claims-Paying Ratings ◦ A.M. Best: “A” (Excellent) ◦ Fitch: “A-” (Strong) • 19 locations, with operations in three countries ◦ 1,086 employees • Writing in 50 states & DC Corporate Headquarters Claims Offices Claims/Underwriting Offices Underwriting Offices Cayman Islands Lloyds

ProAssurance Investor Briefing | June 2023 5 ProAssurance Executive Leadership Ned Rand - President & Chief Executive Officer Mr. Rand became President and CEO in 2019, after serving as COO, CFO, Executive VP, and Senior VP of Finance at ProAssurance since joining the company in 2004. Prior to joining ProAssurance, he served in a number of financial roles for insurance companies. Mr. Rand is a CPA and graduate of Davidson College (B.A., Economics) Executive Team bios available on our website at Investor.ProAssurance.com/OD Kevin Shook President, Workers’ Compensation & Segregated Portfolio Cell Reinsurance Noreen Dishart Executive Vice President & Chief Human Resources Officer Dana Hendricks Executive Vice President & Chief Financial Officer Jeff Lisenby Executive Vice President & General Counsel Karen Murphy President Life Sciences Rob Francis President Healthcare Professional Liability Ross Taubman President Small Business Unit

ProAssurance Investor Briefing | June 2023 6 ProAssurance Board of Directors Director bios available on our website at Investor.ProAssurance.com/OD Maye Head Frei C M. James Gorrie N/C Ziad R. Haydar, MD C Edward L. Rand, Jr E Frank A. Spinosa, DPM N/C Katisha T. Vance, MD N/C A - Audit Committee C - Compensation Committee E - Executive Committee N/C - Nominating/Corporate Governance Committee Underlined - Chair Scott C. Syphax C Samuel A. Di Piazza, Jr A, E Fabiola Cobarrubias, MD A Kedrick D. Adkins, Jr A Thomas A.S. Wilson, Jr, MD N/C Bruce D. Angiolillo Independent Chair E

ProAssurance Investor Briefing | June 2023 7 ProAssurance Brand Profile Specialty P&C Healthcare Professional Liability Workers’ Comp Alternative Risk Transfer Medical Technology & Life Sciences Products Liability Legal Professional Liability

ProAssurance Investor Briefing | June 2023 8 ProAssurance Specialty Property & Casualty • Healthcare Professional Liability (HCPL) insures healthcare providers and facilities, including E&S coverages • The Small Business Unit insures podiatrists, chiropractors, dentists, and lawyers • Medmarc insures medical technology and life sciences companies that manufacture or distribute products Eastern Alliance Workers’ Compensation • Specialty underwriter of workers’ compensation products and services • Focused in the East, South, and Midwest regions of the United States • Guaranteed cost, policyholder dividend, retro-rated, deductible, and alternative solutions policies available Inova Re/Eastern Re SPC Reinsurance • Segregated Portfolio Company structure • Workers’ compensation and healthcare professional liability coverage in a Cayman-based captive • Industries include healthcare, forestry, staffing, construction, petroleum, marine and recreation, and social services Lloyd’s Syndicates • The results from our participation in Lloyd's of London Syndicates. Participation has been reduced to 5% of one syndicate (1729) in the past two years. ProAssurance Corporate • Reports our investment results, interest expense, and U.S. income taxes • Includes corporate expenses and includes non-premium revenues generated outside of our insurance entities • Company-wide administrative departments reside in ProAssurance Corporate ProAssurance Reports Financial Results in Five Segments

ProAssurance Investor Briefing | June 2023 9 ProAssurance Specialty Property & Casualty Specialty Healthcare Life SciencesSmall Business Unit Standard Physicians Healthcare Professional Liability Insurance $42M$101M$427M $205M Gross Premiums Written Last 12 months $817M Specialty Property & Casualty • Deep expertise and broad product spectrum in healthcare and related sciences • Consolidation in HCPL → demand for comprehensive insurance solutions • Small Business Unit → deliver products and services efficiently to the small business healthcare community and related businesses Tail & other Coverages $41M 03/31/2023 Subject to rounding

ProAssurance Investor Briefing | June 2023 10 Disciplined individual account underwriting with focus on rate adequacy in rural territories • Guaranteed Cost Policies • Loss-Sensitive Dividend Plans • Deductible Plans • Retrospective Rating Plans • ParallelPay–“Pay as you Go” • Specialty Risk (high hazard) • Claims Administration and Risk Management Workers’ Compensation Insurance • Wide diversification – over 600 class codes and 32 market segments, primarily in rural territories • Opportunity for organic growth outside of Pennsylvania and Indiana • Proactive claim-closing strategies key to being recognized as a short-tail writer of workers’ compensation o Between 2013 and 2022, averaged approximately 40% faster claims closure rate than industry o 30 claims open from 2015 and prior, net of reinsurance o Pharmacy spend as a percent of medical payments of 3.6% compared to the industry average of 14% • Value-added risk management services and claims/underwriting expertise cement brand loyalty Clubs Banks Restaurants Outside Sales Retirement & Life Care Community Hospitals Auto Dealers Physicians & Dentists Colleges & Schools Clerical & Office 0.0% 2.0% 4.0% 6.0% 8.0% 10.0% 12.0% 14.0% 16.0% *Excludes alternative markets business ceded to the Segregated Portfolio Cell Reinsurance segment Dedicated to effective claims management and returning injured workers to wellness Healthcare Related Non-Healthcare Top 10 Classes of Business by Payroll Exposure (Traditional Business*) as of 12/31/2022

ProAssurance Investor Briefing | June 2023 11 Segregated Portfolio Cell Reinsurance ProAssurance Fronting Arrangement Agency Group or Association establishes a cell Underwriting Claims Administration Risk Management Reinsurance Audit Asset Management Services + Cell Rental Fees + Participation in profits/losses of selected cells Fee Income to PRA • HCPL and workers’ compensation captive insurance solutions through Inova Re (Cayman Islands) • SPCs are a high ROE product with favorable retention results • Low capital requirement • Strategic partnerships with select independent agencies looking to manage controllable expenses • Alternative market solutions are in high demand • Value-added risk management services and claims/underwriting expertise Inova Re Services As of 03/31/2023 • Gross premiums written YTD: $23M o Workers’ Compensation Insurance: $20M o Healthcare Professional Liability: $3M • 23 active cells Individually capitalized cells (companies) exist within the Inova Re structure. Assets of each are segregated from others. ProAssurance/Eastern participates in select cells

ProAssurance Investor Briefing | June 2023 12 • ProAssurance is recognized for our financial strength by top rating agencies • We maintain a balance sheet that ensures stability and security for our customers • Our conservative reserving philosophy enables success over the insurance cycles Financial Ratings & Balance Sheet Highlights Balance Sheet Highlights 03/31/2023 Total Assets $5,747,863 Total Investments $4,381,648 Net Loss Reserves $3,469,279 Total Debt (less Issuance Costs) $427,526 Shareholders’ Equity $1,138,290 Book Value per Share $21.07 Rating Agency Financial Strength Rating Date AM Best A 5/23/2023 Fitch A-* 10/20/2022 Moody’s A3 7/22/2022 $ in thousands, except per share data * Excludes NORCAL Group, which has not yet been rated by Fitch All financial rating information is available on our website: https://investor.proassurance.com/financial-information/financial-ratings/default.aspx

ProAssurance Investor Briefing | June 2023 13 • $428M total debt principal at 03/31/2023 o $178M of Contribution Certificates from NORCAL acquisition o $250M 5.3% 10-year notes due 11/15/2023 • $250M revolving credit facility, $50M "accordion" option, no outstanding borrowing • In April 2023, ProAssurance extended the expiration of its revolving credit agreement, agreed to a delayed draw term loan, and entered into certain swap agreements. We plan to use these to refinance the senior notes due in November 2023. ProAssurance Leverage Update Targeted Premium to Equity ratio is 0.75:1 Financial Leverage – Debt to Capital Operating Leverage – Premiums to Equity 16% 16% 16% 24% 24% 24% $- $0.5 $1.0 $1.5 $2.0 2018 2019 2020 2021 2022 2023 $ in billions Debt Capital Debt to Capital 0.54 0.56 0.55 0.62 0.92 0.87 $- $0.4 $0.8 $1.2 $1.6 2018 2019 2020 2021 2022 2023 $ in billions Net Premiums Written Equity Premiums to Equity

ProAssurance Investor Briefing | June 2023 15 A Foundation in Excellence “From our earliest days, we have operated with a strategy both responsive to near-term challenges and proactive to long-term opportunity.” -Ned Rand President & CEO Superior brand identity and reputation in the market Specialization • Deep expertise and commitment to our customers throughout the insurance cycles enable us to outperform our peers over time Experienced & Collaborative Leadership • Average executive leadership tenure of 20 years with PRA or subsidiaries History of Successful M&A • Selective M&A with best-in-class partners, and nearly 20 transactions in our 47 year history Scope & Scale • Regional hubs combined with local knowledge of market dynamics and regulatory environments

ProAssurance Investor Briefing | June 2023 16 Ex ec u ti n g o u r St ra te gy Enterprise-Wide ➢ Safely and successfully re-opened offices after 2 years of primarily remote work ➢ AM Best and Fitch ratings moved to Stable outlook in 2022 Specialty Property & Casualty ➢ Achieved renewal rate increases of 10% for Specialty Healthcare and 7% for Standard Physicians ➢ Further integrated NORCAL business into legacy operations ➢ Improved retention in the Specialty P&C segment Workers’ Compensation Insurance ➢ Reduced combined ratio by 1.6 points for the year ➢ Closed 62% of 2021 and prior claims during 2022 Corporate Segment ➢ Increased investment income by over $25 million for the year ➢ Streamlined corporate structure by eliminating or merging 5 entities throughout the year 2022 Accomplishments

ProAssurance Investor Briefing | June 2023 17 2 0 2 3 G o al s / In it ia ti ve s SP&C Innovation and Operational Excellence ➢ Launch a state-of-the-art workflow solution across the segment ➢ Build out data science and predictive analytics strategy ➢ Develop and launch a next generation online portal for customers and agents SP&C Product and Program Innovation Working Group ➢ Evaluate new product and program ideas ➢ Consult on new product and program initiatives across Specialty P&C Workers’ Compensation Insurance Strategic Focus ➢ Implement policy, claims, risk management, and billing system ➢ Expand market penetration in “Pay as you Go” and unite (small business) segments Corporate Segment ➢ Increase investment income through investment leverage and reinvesting of portfolio maturities ➢ Execute a defined statutory consolidation strategy ➢ Manage talent-acquisition and retention strategies to build and maintain high-quality talent Strategic Initiatives Drive our Competitiveness

ProAssurance Investor Briefing | June 2023 19 Income Statement Highlights (3/31/23) Three Months Ended March 31 2023 2022 Gross Premiums Written $ 315.8 $ 335.6 Net Premiums Earned $ 239.8 $ 265.7 Net Investment Result $ 29.2 $ 28.1 Net Investment Gains (Losses) $ 2.9 $ (13.5) Total Revenues $ 272.7 $ 283.1 Net Losses and Loss Adjustment Expenses $ 205.3 $ 209.4 Underwriting, Policy Acquisition & Operating Expenses $ 67.8 $ 71.8 Net Income (Loss) (Includes Realized Investment Gains & Losses) $ (6.2) $ (3.6) Non-GAAP Operating Income (Loss) $ (8.1) $ 7.7 Non-GAAP Operating Income (Loss) per Diluted Share $ (0.15) $ 0.14 In millions, except per share data | Subject to rounding

ProAssurance Investor Briefing | June 2023 20 Current Accident Year Net Loss Ratio 87.2 % 85.8 % Effect of Prior Accident Year Reserve Development 4.3 % (2.0%) Net Loss Ratio 91.5 % 83.8 % Underwriting Expense Ratio 22.8 % 21.7 % Combined Ratio 114.3 % 105.5 % Specialty P&C Financial Highlights (3/31/23) Three Months Ended March 31 2023 2022 Gross Premiums Written $ 238.9 $ 257.7 Net Premiums Earned $ 179.3 $ 198.0 Total Revenues $ 180.3 $ 199.0 Net Losses & Loss Adjustment Expenses $ (164.1) $ (166.0) Underwriting, Policy Acquisition & Operating Expenses $ (41.0) $ (42.9) Segment Results $ (24.7) $ (9.9) In millions, except ratios | Subject to rounding

ProAssurance Investor Briefing | June 2023 21 Workers’ Compensation Insurance Financial Highlights (3/31/23) Three Months Ended March 31 2023 2022 Gross Premiums Written $ 73.4 $ 72.1 Net Premiums Earned $ 40.8 $ 40.7 Total Revenues $ 41.4 $ 41.4 Net Losses & Loss Adjustment Expenses $ (30.8) $ (27.2) Underwriting, Policy Acquisition & Operating Expenses $ (13.0) $ (13.0) Segment Results $ (2.4) $ 1.2 Current Accident Year Net Loss Ratio 72.6 % 71.8 % Effect of Prior Accident Year Reserve Development 3.0 % (4.9%) Net Loss Ratio 75.6 % 66.9 % Underwriting Expense Ratio 31.8 % 32.0 % Combined Ratio 107.4 % 98.9 % In millions, except ratios | Subject to rounding

ProAssurance Investor Briefing | June 2023 22 Segregated Portfolio Cell Reinsurance Financial Highlights (3/31/23) Three Months Ended March 31 2023 2022 Gross Premiums Written $ 22,881 $ 28,369 Net Premiums Earned $ 15,300 $ 19,314 Net Investment Income $ 420 $ 112 Net Gains (Losses) $ 1,160 $ (711) Other Income (Loss) $ 1 $ 1 Net Losses & Loss Adjustment Expenses $ (8,423) $ (11,491) Underwriting, Policy Acquisition & Operating Expenses $ (5,035) $ (4,369) SPC U.S. Federal Income Tax Expense $ (532) $ (642) SPC Net Results $ 2,891 $ 2,214 Segregated Portfolio Cell Dividend (Expense)/Income $ (1,942) $ (2,367) Segment Results $ 949 $ (153) In thousands, except ratios | Subject to rounding Current Accident Year Net Loss Ratio 64.9 % 64.5 % Effect of Prior Accident Year Reserve Development (9.8%) (5.0%) Net Loss Ratio 55.1 % 59.5 % Underwriting Expense Ratio 32.9 % 22.6 % Combined Ratio 88.0 % 82.1 %

ProAssurance Investor Briefing | June 2023 23 Lloyd’s Syndicates Segment Financial Highlights (3/31/23) Three Months Ended March 31 2023 2022 Gross Premiums Written $ 3.5 $ 5.8 Net Premiums Earned $ 4.3 $ 7.7 Total Revenues $ 4.5 $ 7.7 Net Losses & Loss Adjustment Expenses $ (2.0) $ (4.8) Underwriting, Policy Acquisition & Operating Expenses $ (1.7) $ (2.7) Segment Results $ 0.8 $ 0.2 Current Accident Year Net Loss Ratio 51.3 % 41.8 % Effect of Prior Accident Year Reserve Development (5.7 %) 19.7 % Net Loss Ratio 45.6 % 61.5 % Underwriting Expense Ratio 39.6 % 35.0 % Combined Ratio 85.2 % 96.5 % In millions, except ratios | Subject to rounding

ProAssurance Investor Briefing | June 2023 24 Corporate Segment Financial Highlights (3/31/23) Three Months Ended March 31 2023 2022 Net investment income $ 29.7 $ 20.1 Equity in earnings (loss) of unconsolidated subsidiaries $ (1.1) $ 7.6 Net investment gains (losses) $ 0.8 $ (12.4) Other income $ 0.3 $ 2.1 Operating expenses $ 8.2 $ 8.7 Interest expense $ 5.5 $ 4.4 Income tax expense / (benefit) $ (2.2) $ (1.8) Segment results $ 18.2 $ 6.0 In millions | Subject to rounding

ProAssurance Investor Briefing | June 2023 25 YTD 2023 Net Investment Result and Equity Rollforward Data shown in thousands 2023 Beginning Equity $1,104,018 Employee Stock Transactions 518 Earnings (6,174) Dividends (2,701) Unrealized G/L 42,629 Total Equity $1,138,290 ($ in millions) 3/31/2023 3/31/2022 Change Net Investment Income Fixed maturities $ 27,327 $ 21,544 $ 5,783 Equities 807 701 106 Short-term investments including Other 3,350 426 2,924 BOLI 657 (47) 704 Investment fees and expenses (1,831) (2,181) 350 Net investment income 30,310 20,443 9,867 Equity in Earnings (Loss) of Unconsolidated Subsidiaries All other investments, primarily investment fund LPs/LLCs (767) 10,008 (10,775) Tax credit partnerships (354) (2,388) 2,034 Equity in earnings (loss) (1,121) 7,620 (8,741) Net investment result $ 29,189 $ 28,063 $ 1,126

ProAssurance Investor Briefing | June 2023 26 Lloyd’s of London Syndicates ProAssurance Funds at Lloyd’s (FAL) $25.1 Million 1 Property Insurance (All Other - Mainly US) 28% Casualty (Mainly US) 28% Catastrophe Reinsurance (Excess of Loss) 15% Specialty 8% Facility (US) 6% General Liability (US) 4% Contingency 5% All Other Reinsurance (Mainly US) 6% 2022 Premium Distribution Dale Underwriting Partners Independent, Owner-Managed Syndicate at Lloyd’s Syndicate 1729 PRA participation 5% PRA share of 2023 underwriting capacity $19M • Invest alongside a recognized leader in Duncan Dale • Lloyd’s provides universal distribution and licensures • Westernization of international healthcare professional liability provides opportunities in new markets 1 Comprised of investment securities, cash, and cash equivalents deposited with Lloyd's as of 03/31/2023. 2 For the 2022 underwriting year, and effective January 1, 2022, Syndicate 6131 ceased underwriting on a quota share basis with Syndicate 1729. Its business will be retained within Syndicate 1729. Due to the quarter lag, this was first reflected in our results in Q2 2022. Subject to rounding Premium percentages reflect 100% of the Syndicates’ premiums written, and not solely ProAssurance’s participation.

ProAssurance Investor Briefing | June 2023 27 Investment Philosophy & Portfolio Total Investments $4.38 Billion 03/31/2023 Subject to rounding Details of our investment portfolio are available on our website at https://investor.proassurance.com/financial-information/quarterly-investment-supplements/default.aspx 30% 12% 10%9% 8% 6% 7% 6% 5% 3% 4% AAA A A+ BBB+ Below Investment Grade or Not Rated BBB A- AA- AA AA+ BBB- Fixed Maturity Credit Quality Portfolio Statistics 1Q23 1Q22 Avg Income Yield 2.9% 2.3% Wtd Avg Duration 3.41 3.78 Commentary • Effective stewardship of capital ensures a position of financial strength through turbulent market cycles • Optimizing our allocations for better risk-adjusted returns. Ensures non-correlation of returns • Ongoing analysis of holdings to ensure lasting quality and profitability ABS 23% BOLI 2% Bond Funds 3% Corporate 40% Fixed Maturies Trading 1% Other 2% Short Term 7% Private Equity 3% Private Credit 3% State/Muni 10% Real Estate 1% US Govt/Agency 6% 6

ProAssurance Investor Briefing | June 2023 28 Combined Tax Credits Portfolio Detail & Projections The total credits column represents our current estimated schedule of tax credits that we expect to receive from our tax credit partnerships. The actual amounts of credits provided by the tax credit partnerships may prove to be different than our estimates. These tax credits are included in our Tax Expense (Benefit) on our Income Statement (below the line) and result in a Tax Receivable (or a reduction to a Tax Liability) on our Balance Sheet. GAAP Income/(Loss) Tax Provision Impact on from Operations, after Impairment Earnings Disposition & Impairment 2023 $ 51,338 (3,315,731) (371,517) (1,067,819) (2,247,913) 2024 $ 51,338 (1,589,628) (38,350) (372,171) (1,217,457) 2025 $ 41,159 (766,868) (21,466) (182,508) (584,360) 2026 $ 25,734 (172,836) (2,684) (38,980) (133,857) 2027 $ - (635,790) 7 (133,508) (502,282) 2028 $ - - - - - Year Capital Total Credits Contributions

ProAssurance Investor Briefing | June 2023 29 Forward Looking Statements Non-GAAP Measures This presentation contains Forward Looking Statements and other information designed to convey our projections and expectations regarding future results. There are a number of factors which could cause our actual results to vary materially from those projected in this presentation. The principal risk factors that may cause these differences are described in various documents we file with the Securities and Exchange Commission, such as our Current Reports on Form 8-K, and our regular reports on Forms 10-Q and 10-K, particularly in “Item 1A, Risk Factors.” Please review this presentation in conjunction with a thorough reading and understanding of these risk factors. This presentation contains Non-GAAP measures, and we may reference Non-GAAP measures in our remarks and discussions with investors. The primary Non-GAAP measure we reference is Non-GAAP operating income (loss), a Non-GAAP financial measure that is widely used to evaluate performance within the insurance sector. In calculating Non-GAAP operating income (loss), we have excluded the after-tax effects of net realized investment gains or losses and guaranty fund assessments or recoupments that do not reflect normal operating results. We believe Non-GAAP operating income presents a useful view of the performance of our insurance operations, but should be considered in conjunction with net income (loss) computed in accordance with GAAP. A reconciliation of these measures to GAAP measures is available in our regular reports on Forms 10-Q and 10-K and in our latest quarterly news release, all of which are available in the Investor Relations section of our website, Investor.ProAssurance.com. IMPORTANT SAFE HARBOR & NON-GAAP NOTICES

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