#1OLD REPUBLIC MANAGING OLD REPUBLIC FOR THE LONG RUN Investor Presentation 4th Quarter 2023#2OLD REPUBLIC Preliminary Matters Forward Looking Statements This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. The words “expect,” “estimate,” “anticipate," "predict" and similar expressions, and the negatives thereof, often identify forward-looking statements, which are not limited to historical facts. Forward-looking statements include, among other things: future guidance; projected annual revenues resulting from new or existing products or services; dividends; statements, express or implied, concerning future operating results, the ability to generate premium, income or cash flow; and Old Republic's business and growth strategies and expected growth and performance. Although Old Republic believes these statements are based upon reasonable assumptions, they involve risks and uncertainties relating to operations, markets and the business environment generally. If one or more of these risks or uncertainties materializes, or underlying assumptions prove incorrect, actual outcomes may vary materially from those indicated. Readers are advised to consult further disclosures on these risks and uncertainties, particularly in Item 1A, "Risk Factors", of Old Republic's Annual Report on Form 10-K for the year ended December 31, 2022 and in its subsequent filings with the Securities and Exchange Commission. All forward-looking statements included in this presentation are based upon information available, and it assumes no obligation to update them. Non-GAAP Financial Measures This presentation provides information which includes certain financial measures that are not in accordance with U.S. generally accepted accounting principles ("GAAP"). Management discloses non-GAAP information to provide investors with additional information to analyze Old Republic's performance and underlying trends. Management uses non-GAAP measures that exclude certain items in order to better assess operating performance and help investors compare results with our previous performance. Old Republic's non-GAAP information is not necessarily comparable to the non-GAAP information used by other companies. Non-GAAP information should not be viewed as a substitute for, or superior to, net income or other data prepared in accordance with GAAP as a measure of Old Republic's profitability or financial position. Readers should consider the types of events and transactions for which adjustments have been made. 2#3OLD REPUBLIC Managing Old Republic for the Long Run Primarily a Specialty underwriter serving the insurance needs of a large number of organizations, including Property & Casualty provider to many of America's leading industrial and financial services institutions and provider of Title Insurance to America's residential and commercial markets A history dating back 100 years Total Market Return of 12.6% per share for past 10 years NYSE listed since 1990 Member of the Fortune 500 listing of America's largest companies One of America's 50 Largest shareholder-owned insurance businesses #3 Title insurer in the nation 82 years of cash dividends without interruption Annual cash dividend raised for each of the past 42 years $4.2 billion of dividends & share repurchases since 12.31.16 3#4OLD REPUBLIC Key Metrics Market Cap / Stock price (NYSE: ORI) Shareholders' Equity / BVPS $6.41 billion / $23.31 Trailing 4 Quarter Operating Income / EPS $749.5 million / $2.63 $8.18 billion / $29.40 A+ SUPERIOR Financial Strength Rating BEST A+ Superior 12.1% Trailing 4 Quarter Operating ROE Regular Dividend / Yield $0.98 / 3.3% Employees 9,200 Insider and Employee Ownership 8.8% Note: Market and financial data as of December 31, 2023 A+ STRONG S&P Global 4#5OLD REPUBLIC Shareholder Returns are Driven by Our Long-Term Focus Operating and growing a diverse & decentralized portfolio of specialty insurance products and services Pursuing operational & underwriting excellence through narrow & deep expertise Fostering a unique culture built around integrity, respect and accountability Driving deep relationships built on outstanding customer service and risk management expertise Investing in people and technology Aligning incentives and accountability to drive profitable growth Maintaining a lean and flat organizational structure 5#6OLD REPUBLIC Consolidated Financial Trend Dollars in millions, except per share 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 Total Operating Revenues $ 5,407 $ 5,850 $ 6,032 $ 6,281 $ 6,494 $ 6,824 $ 7,308 $ 8,583 $ 8,285 $ 7,449 Combined Ratio 99.4 96.1 94.8 96.9 94.9 95.3 93.3 89.9 91.0 92.6 Operating Income Per Share $ 0.84 $ 1.28 $ 1.46 $ 1.11 $ 1.86 $ 1.84 $ 2.24 $ 3.08 $ 2.79 $ 2.63 Cash & Invested Assets $ 11,291 $ 11,476 $ 12,996 $ 13,536 $ 13,187 $ 14,527 $ 15,535 $ 16,819 $ 16,048 $ 16,188 Shareholders' Equity $ 3,924 $ 3,870 $ 4,461 $ 4,733 $ 5,146 $ 6,000 $ 6,187 $ 6,895 $ 6,173 $ 6,411 Book Value Per Share (BVPS) $ 15.15 $ 14.98 $ 17.16 $ 17.72 $ 17.23 $ 19.98 $ 20.75 $ 22.77 $ 21.07 $ 23.31 Dividends Per Share (1) $ 0.73 $ 0.74 $ 0.75 $ 1.76 $ 0.78 $ 1.80 $ 1.84 $ 2.38 $ 1.92 $ 0.98 (1) Includes special cash dividends declared of $1.50 in 2021 and $1.00 in 2022, 2020, 2019 and 2017 $50 $45 12.1% Compound Annual Growth in Book Value Per Share Including Dividends over 50 years $40 $35 $30 $25 $20 $15 $10 $5 $- 1973 1978 1983 1988 1993 1998 2003 2008 2013 2018 2023 ■BVPS ■Cumulative Dividends 6#7OLD REPUBLIC 4th Quarter 2023 Highlights $0.69 Operating EPS 14% decrease from $0.80 in the 4th quarter of 2022 driven by 19% pretax operating income decline in General Insurance and a 3% decline in Title Insurance. $23.31 Book Value Per Share Adding back dividends, book value increased 15.3% from year-end 2022. $1.74 billion Net Premiums & Fees Earned 93.3 Combined Ratio 5% decrease driven by Title Insurance (down 23%) offset by General Insurance (up 11%). Up 3.7 points versus last year's 89.6. General Insurance at 92.0 (vs 84.0) and Title Insurance at 95.5 (vs 96.2). 4.6 points Favorable Development $0.245 Regular Quarterly Dividend Favorable development in all segments. Up 6.5% from prior year $55 million Share Repurchases Completed in 4th quarter under current $450 million authorization. $530 million repurchased year-to-date. 7#8OLD REPUBLIC Business Profile Unique and complimentary combination of Specialty P&C and Title offers diversification and supports our brand around customer service, financial strength, underwriting & trust OLD REPUBLIC GENERAL INSURANCE GROUP OLD REPUBLIC TITLE INSURANCE GROUP General Insurance $4.7 billion of 2023 operating revenue ☐ Capital heavy High loss-low expense Highly diverse competitors P&C market cycle influenced Title Insurance $2.6 billion of 2023 operating revenue Capital light Low loss-high expense 3rd largest in concentrated industry Real estate market cycle influenced General Insurance 84% Title Insurance 14% 8 Based on 2023 Pre-Tax Operating Income#9OLD REPUBLIC A history of launching and acquiring specialty businesses Date of start-up or acquisition T 1973 $71 Old Republic Canada Old Republic Title Insurance Group $78 I 1978 $83 Old Republic Aerospace Old Republic Home Protection $81 1983 I $85 BITCO & Great West Casualty Company Old Republic Professional 1988 $83 1993 Old Republic Surety $85 Old Republic Risk Management $86 1998 $92 Old Republic Insured Automotive Services 2003 | 2008 PMA $10 2013 $15 Old Republic Specialty Insurance Underwriters Old Republic Residual Market Services $18 2018 $21 Old Republic Inland Marine 2023 Old Republic Excess & Surplus $22 I $23 Old Republic Accident & Health Old Republic Lawyers Specialty Insurance Company $23 9#10OLD REPUBLIC General Insurance – Profile - Our business model emphasizes diversification to mange risk and decentralization to foster industry specialization, autonomy & accountability ORINSCO Includes large national accounts with customers taking risk through captives and large deductibles; also includes Automotive Services, Aerospace and Professional Liability $6.87 billion Gross premiums + fees (FY 2023) Great West Commercial auto, workers' compensation, physical damage and cargo for the trucking industry, including accounts with customers taking risk through captives and large deductibles. PMA TPA services, workers' compensation and other coverages for large and mid-sized companies, including accounts with customers taking risk through captives, large deductibles and retrospectively rated policies ORINSCO 37% Other Specialty Products Specialty Ins. Underwriters, Home Protection, Canada, Surety, Residual Markets and recent startups Inland Marine, Excess & Surplus, Lawyers Specialty and Accident & Health Great Other Specialty 19% West 25% PMA BITCO 8% 11% BITCO Coverage for the forest, oil & gas and construction industries; primarily workers' compensation, GL and commercial auto, including accounts with customers taking risk through large deductibles 10#11OLD REPUBLIC General Insurance - Differentiation The General Insurance Segment's specialty business model includes over 70 years of Risk Management expertise serving large customers and group clients The Product ☐ Customers share in underwriting risk Key Loss Sensitive Structures: Retrospective rated programs Large deductibles ■ Captives Self-insured retentions □ Old Republic provides administrative & underwriting services that are difficult to replicate ☐ Credit exposure managed through collateralization of risk The Result ✓ High (90%+) customer retention ✓ Less commoditized ✓ Less cyclical ✓ Consistent growth ✓ Financial alignment with insureds Driving Risk Management Expertise 70% of workers' compensation premium is loss sensitive BITCO INSURANCE COMPANIES GREAT WEST CASUALTY COMPANY OLD REPUBLIC RISK MANAGEMENT OLD REPUBLIC SPECIALTY INSURANCE UNDERWRITERS, INC. PMA COMPANIES 11#12OLD REPUBLIC General Insurance - Premium The General Insurance segment has achieved sustained growth and stable underwriting profitability Long-term growth with a willingness to contract when rate levels are inadequate ☐ Specialty niches through agent & broker distribution Customer service orientation across 115 local offices ☐ Approximately 72% casualty; 28% short-tailed lines ☐ Relatively low property-cat exposure; protected by reinsurance Net Premium Earned Other, 7% $4.50 Home and Auto Warranty, 8% $4.12 $4.00 $3.50 Inland Marine & CMP, 11% Commercial auto (principally trucking), 41% $3.00 Billions $2.50 $2.00 $1.50 Financial Indemnity, 8% $1.00 Workers Compensation, 19% $0.50 General Liability, 6% $- 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Based on YE 2023 data 12#13OLD REPUBLIC General Insurance – Underwriting Profit The General Insurance segment has proven consistently profitable and resilient across market cycles Combined Ratio ☐ Combined ratios below industry by an average of 5.3 points over 15 years ☐ 14 of 15 years below a 100 combined ratio; 96 average over 15 years; targeting 90-95 Pretax Operating Income General Insurance segment is a significant and consistent driver of income 95.6 94.7 94.4 98.7 97.3 100.8 97.6 97.8 97.3 97.2 97.5 95.5 91.3 89.5 90.2 $1,000 $900 $800 $700 $600 Millions $500 $400 $300 $200 $100 $- 17 18 19 20 21 22 23 $(100) Expense Ratio 09 10 11 12 13 14 15 16 Loss Ratio 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 13 $788#14Billions $5.0 OLD REPUBLIC Title Insurance - Profile The Title Insurance segment has continued a long-run trend of profitable growth ☐ #3 in a concentrated industry ☐ Lower capital requirements $1.0 billion in equity at Dec. 31, 2023 supporting $2.6 billion of revenue (2.6x) ☐ 2023 revenue from agency (79%) and direct operations (21%) through 270 offices ☐ Continuing to expand presence in commercial real estate market (22% of 2023 premiums) Title Revenue Title Market Share Old Republic 15.1% $4.5 $4.0 $3.5 Fidelity National (FNF) 30.7% $3.0 $2.5 $2.0 $1.5 $1.0 $2.6 First American (FAF) 25.5% Other 18.3% Stewart Title (STC) 10.4% $0.5 $- 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Source: American Land Title Association at 09/30/23 14#15OLD REPUBLIC Title Insurance - Differentiation The Title Insurance segment brings together a focus on independent agency distribution and proprietary title technology Agency Focused Distribution ☐ Strategic focus on independent title agents that control 64% of industry premium Delivering tools, technology & support to drive agent success Partnership - not competition - with agents ☐ Scalability in all market conditions with expense "downside" protected in soft markets Industry Distribution Strategic Focus 21% Market Share Agency, 64.0% Direct, 36.0% 5% Market Share Proprietary "Title Tech" pavāso Source: 09/30/23 ALTA As a leader in digital mortgage transformation, Old Republic's Pavaso enables fully digital and hybrid eClosings through one secure collaborative platform that streamlines the entire closing process RO RamQuest E-Closing RECORDING PARTNERS ePN NETWOR Old Republic's Title Tech portfolio includes platforms to empower the real-estate ecosystem with cloud-based closing, escrow, accounting, recording and transaction management solutions to modernize and streamline title operations 15#16OLD REPUBLIC Title Insurance - Profit Consistently low single-digit loss ratios and a variable cost structure have enabled consistent profitability Combined Ratio Low and consistent loss ratios ■ 94.9% average last 15 years Pretax Operating Income ☐ Overweight in agency distribution ■ Variable acquisition cost mitigates impact of a real estate market decline 105.0 $600 100.0 $500 97.1 95.0 $400 90.0 85.0 Millions $300 $200 $134 80.0 $100 75.0 $- 70.0 $(100) 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Expense Ratio Loss Ratio 16#17OLD REPUBLIC Balance Sheet, Liquidity & Capital Overview Strong capital position marked by a high quality and conservative balance sheet High quality, liquid portfolio Bonds & Stocks. No ‘alternatives' Strong reserve position Conservative reserving & favorable development High quality capital Limited goodwill & intangibles (3% of capital) Release of run-off capital $163 million of shareholders equity at 4Q23 Parent company liquidity Share repurchases Subsidiary dividend capacity of $925 million in 2023 $530 million repurchased (20.9 million shares) in 2023 17#18OLD REPUBLIC Dividend Record Shareholder friendly dividend track record through all business and market cycles ☐ $0.98 annual regular dividend ($0.245/quarter) Paid dividends 82 consecutive years ☐ Annual dividend increases for 42 consecutive years $1.10 $1.00 Regular Dividends Special Dividends $1.50 $1.50 $0.98 $1.25 $1.00 $1.00 $1.00 $1.00 $1.00 $0.75 $0.50 $0.25 $0.90 $0.80 $0.70 $0.60 $0.50 12 13 14 15 16 17 18 19 20 21 22 223 17 18 19 20 20 21 21 22 22 18#19OLD REPUBLIC Investment Portfolio The investment portfolio is high-grade, transparent and liquid Fixed Income 99% Investment grade A+ average quality 3.7 duration 4.7% market yield (4.0% book yield) 99% marketable securities Investment Mix at 4Q23 $15.8 O 83% billion 17% Equities Blue Chip, Value & Utilities 3.4% dividend yield Approximately 75 issuers No exposure to real estate, CDOs, derivatives, hybrids or illiquid private equity and hedge fund investments Investment Income Millions $700 $600 $500 $400 $300 $200 $578 2015 2016 2017 2018 2019 2020 2021 2022 2023 19#20OLD REPUBLIC Reserve Development Reserve development has been favorable in each segment Each segment had favorable development each of the last three years (Favorable)/Unfavorable Development % of Net Premiums & Fees Earned 8.0% ☐ On a consolidated basis, 6.0% reserves have developed 4.0% favorably in 9 of the last 10. years 2.0% 0.0% ☐ Disciplined and conservative reserving is a core element of -2.0% ORI's strategy -4.0% -6.0% -8.0% 14 15 16 17 18 19 20 20 21 221 IT 22 22 23 23 20#21OLD REPUBLIC The Lodestar Embodies our Mission by Binding Organization, Purpose and Long-Term Strategy Into a Coordinated Whole Our Community: The Public Interest We're an insurance business vested with the public interest. All is done right, within the law, and with integrity. Old Republic's Lodestar Our Customers: Policyholders & Buyers of Services Good things happen when customers' legitimate needs are fulfilled by our people. Our Community R Our Customers Our People Our Capital Providers: Shareholders & Debt Holders Capital is the lifeblood of a financial institution. It is the source and continuity of the enterprise. Our Capital Providers Our People: Intellectual Capital Providers Our people's intellectual talent, know-how, and honorable work put capital to efficient use. 21#22OLD REPUBLIC Old Republic's Culture, Operating Philosophy, and Institutional Memory It starts with "we". we have each other's back We are efficient - we optimize better and faster We are humble - but we are confident We are patient and thoughtful - we don't panic or overreact We act with integrity - we are trustworthy and honest We do things the right way - we don't follow undisciplined competition We leave politics to politicians - we are collaborative and collegial We are creative and innovative - we think outside the box We are inclusive - we listen to and respect others' points of view We keep things simple - we don't over-engineer and over-analyze We drive out bureaucracy when we see it - our organizational structures are flat We drive down decision making and accountability - we are decentralized We communicate in an open, clear, consistent, concise manner - we tell it like it is We are long-term focused - we don't let short-term or quarterly results guide us 22