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©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 3rd Quarter 2026 Investor Presentation
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2 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Managing Old Republic for the Long Run EXCELLENCE IS OUR SPECIALTY 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. OUR STRENGTH IN NUMBERS A history dating back 103 years Total Shareholder Return of 17.0% per share for past 10 years NYSE listed since 1990 Member of the Fortune® 500 listing of America’s largest companies #3 Title insurer in the nation 85 years of dividends without interruption Annual dividend raised for each of the past 45 years $7.5 billion of dividends & share repurchases since the beginning of 2017
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3 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Key Metrics Market Cap / Stock price (NYSE: ORI) $8.95 billion / $37.31 Shareholders’ Equity / BVPS $5.88 billion / $24.65 Trailing 4-Quarter Operating Income / EPS (a) $722.6 million / $2.91 Operating ROE (b) 12.1% Regular Dividend / Yield $1.26 / 3.4% Employees 9,500 Insider and Employee Ownership 7.6% FORTUNE® 500 NYSE LISTED ORI AM BEST A + S&P GLOBAL A + SUPERIOR STRONG Note: Market and financial data as of September 30, 2026, except Regular Dividend / Yield which has been updated to reflect the current year run-rate. (a) A reconciliation to the most directly comparable GAAP measure is included in the appendix. (b) Operating return on equity (ROE) has been calculated as annual(ized) net operating income as a percentage of common shareholders' equity at the beginning of the year.
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4 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Shareholder Returns are Driven by Our Long-Term Focus Operating and growing a diverse & decentralized portfolio of specialty insurance products and services Combining operational & underwriting excellence with 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, technology and growth initiatives Aligning incentives and accountability to drive profitable growth Maintaining a lean and flat organizational structure
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5 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Consolidated Financial Trends Dollars in millions, except per share 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 Total Operating Revenues $ 6,032 $ 6,281 $ 6,494 $ 6,824 $ 7,308 $ 8,583 $ 8,285 $ 7,449 $ 8,162 $ 8,957 Combined Ratio 94.8 96.9 94.9 95.3 93.3 89.9 91.0 92.6 93.9 94.7 Operating Income Per Share (a) $ 1.46 $ 1.11 $ 1.86 $ 1.84 $ 2.24 $ 3.08 $ 2.79 $ 2.63 $ 3.03 $ 3.15 Cash & Invested Assets $ 12,996 $ 13,536 $ 13,187 $ 14,527 $ 15,535 $ 16,819 $ 16,048 $ 16,188 $ 16,409 $ 17,243 Shareholders’ Equity $ 4,461 $ 4,733 $ 5,146 $ 6,000 $ 6,187 $ 6,895 $ 6,173 $ 6,411 $ 5,619 $ 5,914 Book Value Per Share (BVPS) $ 17.16 $ 17.72 $ 17.23 $ 19.98 $ 20.75 $ 22.77 $ 21.07 $ 23.31 $ 22.84 $ 24.21 Dividends Declared Per Share (b) $ 0.75 $ 1.76 $ 0.78 $ 1.80 $ 1.84 $ 2.38 $ 1.92 $ 0.98 $ 3.06 $ 3.66 (a) A reconciliation to the most directly comparable GAAP measure is included in the appendix. (b) Includes special dividends declared of $2.50 in 2025, $2.00 in 2024, $1.00 in 2022, $1.50 in 2021 and $1.00 in 2020, 2019, and 2017. 14.0% COMPOUND ANNUAL GROWTH IN BOOK VALUE PER SHARE INCLUDING DIVIDENDS OVER 50 YEARS BVPS Cumulative Dividends 1975 1980 1985 1990 1995 2000 2005 2010 2015 2020 2025 $— $10 $20 $30 $40 $50 $60
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6 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 10-Year Growth in BVPS 10-Year Coefficient of Variation 5.0% 6.0% 7.0% 8.0% 9.0% 10.0%11.0% 12.0%13.0%14.0%15.0% —% 50% 100% 150% 200% 250% Low Volatility Model Conservatism, diversification, and risk-sharing structures drive consistency in growth of Book Value Per Share (BVPS). • Limited property-cat exposure • Use of reinsurance to reduce volatility • Diverse product portfolio • Prevalent use of risk-sharing structures • Conservative reserving practices • Consistent investment income Coefficient of variation = standard deviation of annual growth in BVPS divided by the average annual growth in BVPS over 10 years. Growth in BVPS includes dividends. Data through December 31, 2025. P&C Peers = ACGL, AFG, AXS, CB, CNA, CINF, HIG, MKL, SIGI, THG, TRV, WRB Growth in BVPS vs. Variation Operating ROE Strong returns + Low volatility ORI 16 17 18 19 20 21 22 23 24 25 —% 4.0% 8.0% 12.0% 16.0%
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7 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 3rd Quarter 2026 Highlights 6.0% decrease from $0.78 in the 3rd quarter of 2025 driven by 1.8% pretax operating income decrease in Specialty Insurance offset by a 10.1% increase in Title Insurance. 8.8% increase from the 3rd quarter of 2025 driven by Specialty Insurance (up 9.7%) and by Title Insurance (up 7.3%). Up 0.8 points vs last year’s 95.3. Specialty Insurance at 96.0 (vs. 94.8) and Title Insurance at 96.1 (vs. 96.4). Adding back dividends, book value increased 5.7% from year-end 2025. Favorable development in all segments. $521 million remains authorized for repurchases. $0.73 Operating EPS (a) $2.27 billion Net Premiums & Fees Earned 96.1 Combined Ratio $24.65 Book Value Per Share 1.1% points Favorable Development $0.315 Regular Quarterly Dividend (a) A reconciliation to the most directly comparable GAAP measure is included in the appendix. Up 8.6% from 3rd quarter of 2025. $113 million Share Repurchases
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8 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 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. Specialty insurance • $6.0 billion of 2025 operating revenue • Capital heavy • High loss – low expense • Highly diverse competitors • P&C market cycle influenced • Higher interest rates can increase investment income Title insurance • $2.9 billion of 2025 operating revenue • Capital light • Low loss – high expense • Third largest in concentrated industry • Real estate market cycle influenced • Lower interest rates can increase revenue Based on 2025 Pre-Tax Operating Income Specialty Insurance 87% Title Insurance 13%
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9 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. A History of Launching and Acquiring Specialty Businesses Note: Year indicates date of start-up or acquisition.
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10 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Specialty Insurance – Profile Our business model emphasizes diversification to manage risk and decentralization to foster industry specialization, autonomy & accountability. $8.5B Direct Premiums Written (FY 2025) Old Republic Insurance Company Includes large national accounts with customers taking risk through captives and large deductibles; also includes Auto Warranty, Aerospace, and Professional Liability Great West, An Old Republic Company Commercial auto, workers’ compensation, physical damage and cargo for the trucking industry, including accounts with customers taking risk through captives and large deductibles Old Republic Commercial Risk 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 Other Specialty Products Alternative Markets, Home Warranty, Canada, Surety, Residual Markets and recent startups Inland Marine, Excess & Surplus, Lawyers Professional, and Accident & Health Old Republic Bitco Coverage for the forest, oil & gas and construction industries; primarily workers’ compensation, general liability, and commercial auto, including accounts with customers taking risk through large deductibles Old Republic Insurance Company 38.8% Other Specialty 18.1% Bitco 7.6%Commercial Risk 12.0% Great West 23.5%
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11 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Specialty Insurance – Differentiation The Specialty Insurance segment’s 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 72% of workers’ compensation premium is loss sensitive. • Old Republic Bitco • Great West, An Old Republic Company • Old Republic Commercial Risk • Old Republic Alternative Markets • Old Republic Risk Management
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12 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Commercial Auto (principally trucking) 42% Workers' Compensation 17%General Liability 8% Financial Indemnity 7% Inland Marine & CMP 13% Home and Auto Warranty 7% Other 6% Specialty Insurance – Premium The Specialty 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 over 100 local offices • Approximately 74% casualty; 26% short-tailed lines • Relatively low property-cat exposure; protected by reinsurance Net Premium Earned Based on YE 2025 data Billions $5.4 17 18 19 20 21 22 23 24 25 LTM $— $1.00 $2.00 $3.00 $4.00 $5.00 $6.00
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13 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Specialty Insurance – Underwriting Profit The Specialty Insurance segment has proven consistently profitable and resilient across market cycles. Combined Ratio Pretax Operating Income Targeting 90-95 combined ratios over the long run Specialty Insurance segment is a significant and consistent driver of income 97.3 97.2 97.5 95.5 91.3 89.5 90.2 92.2 93.2 95.4 17 18 19 20 21 22 23 24 25 9M26 70 75 80 85 90 95 100 105 Millions $790 17 18 19 20 21 22 23 24 25 LTM $0 $100 $200 $300 $400 $500 $600 $700 $800 $900 $1,000
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14 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Title Insurance – Profile ORI’s Title Insurance business is the 3rd largest in this concentrated industry with 14.0% market share. • Lower capital requirements • $1.0 billion in equity at Dec. 31, 2025, supporting $2.9 billion of premium & fees (2.9x) • 2025 premium from independent title agents is 78% of total premium & fees • 246 local offices to serve customers • Strong presence in commercial real estate market (26% of 2025 premiums) Title Revenue Title Market Share Source: American Land Title Association at 12/31/25 Billions $3.1 17 18 19 20 21 22 23 24 25 LTM $0.0 $0.5 $1.0 $1.5 $2.0 $2.5 $3.0 $3.5 $4.0 $4.5 $5.0 Old Republic 14.0% Stewart Title (STC) 11.2% Other 17.2% First American (FAF) 25.9% Fidelity National (FNF) 31.7%
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15 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Title Insurance – Differentiation A strategic focus on delivering business solutions and support services for independent title agents. Agency Focused Distribution Agent Support Tools • Strategic focus on independent title agents that control 63% of industry premium • Partnership – not competition – with agents • Delivering products and tools that empower agents to streamline operations, save time, and enhance client experience StarsLink Agent Portal • Equips agents with essential tools and resources • Features comprehensive rate calculators, an online jacket for policy coverage, and supports electronic remittance for efficient financial transactions. • Benefits include closing protection letters, high liability services, and a variety of forms and best practices, making StarsLink an all- inclusive platform Business Solutions and Services • Supporting our agents’ growth and success with a suite of tailored business solutions and services • Customized marketing support, online continuing education, social media management, title search production, and submission of electronic document recordings • Dedicated Commercial Agency Services group to assist agents as a single point of contact with multistate projects • Strategic technology partnerships including with Qualia to deliver digital closing solutions and with CertifID for wire fraud protection Industry distribution Strategic Focus 19% Market Share 5% Market Share Source: 6/30/26 ALTA Agency 63% Direct 37%
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16 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Title Insurance - Profit Consistently low single-digit loss ratios and a variable cost structure help protect profitability in a slow real estate market. Combined Ratio Pretax Operating Income Targeting 90-95 combined ratios over the long run Overweight in agency distribution • Variable acquisition cost mitigates impact of a real estate market decline 91.8 92.8 93 90.7 89.3 93.2 97.1 97 97.6 96.9 17 18 19 20 21 22 23 24 25 9M26 70 75 80 85 90 95 100 105 Millions $189 17 18 19 20 21 22 23 24 25 LTM $0 $100 $200 $300 $400 $500 $600
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17 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 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 (4% of capital) Parent company liquidity Subsidiary dividend capacity of $985 million in 2026 Share repurchases $521 million remains authorized for repurchases
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18 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. $1.00 $1.00$1.00 $1.50 $1.00 $2.00 $2.50 17 18 19 20 21 22 23 24 25 $0.00 $0.50 $1.00 $1.50 $2.00 $2.50 Dividend & Repurchase Record Shareholder friendly dividend track record through all business and market cycles. • $1.26 annual regular dividend run-rate • Paid 85 consecutive years • Annual increases for 45 consecutive years • $10.00 in special dividends since 2017 • $2.21 billion in share repurchases since 2022; just over 24% of shares outstanding Regular Dividends Special Dividends Repurchases ($M) Special dividends are reflected in the year declared. $281 $530 $942 $124 $335 22 23 24 25 9M26 $— $200 $400 $600 $800 $1,000 $1.26 17 18 19 20 21 22 23 24 25 Run- rate $0.00 $0.20 $0.40 $0.60 $0.80 $1.00 $1.20 $1.40
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19 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. 14%86% Investment Portfolio The investment portfolio is high-grade, transparent and liquid Investment Mix at 3Q26 Investment Income Fixed Income Equities • 99% Investment grade • "A" average quality • 3.9 duration • 5.5% market yield (4.9% book yield) • Blue Chip, Value & Utilities • 3.0% dividend yield • Diversified portfolio No exposure to real estate, CDOs, derivatives, hybrids or illiquid private equity and hedge fund investments$16.6 BILLION Millions $729 17 18 19 20 21 22 23 24 25 LTM $300 $400 $500 $600 $700
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20 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Reserve Development Reserve development has been favorable on a consolidated basis. • Each segment had favorable development each of the last five years • On a consolidated basis, reserves have developed favorably each of the last 10 years • Disciplined and conservative reserving is a core element of Old Republic’s strategy (Favorable)/Unfavorable Development – % of Net Premiums & Fees Earned (0.9)% 17 18 19 20 21 22 23 24 25 9M26 (6.0)% (4.0)% (2.0)% —% 2.0% 4.0% 6.0%
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21 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Appendix
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22 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Flagship Case Study: Great West, An Old Republic Company Premier provider of insurance products & services for truckers. • $2.0 billion in direct written premium • Single unit owner-operators to large fleets • Consistently outperforms industry on key metrics A P P E N D I X Statutory Combined Ratio Product Mix Differentiated by: Pricing precision & data/analytics Value-focused agency partnerships Highly specialized products, claims, underwriting & risk control Source: Statutory financial statements Based on YE 2025 data Auto Liability 58% Workers' Comp 4% Physical Damage 26% Cargo 7% General Liability 5% 16 17 18 19 20 21 22 23 24 25 80 85 90 95 100
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23 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Flagship Case Study: Old Republic Risk Management Premier service provider and insurer to large corporate and group insureds. • $2.4 billion in direct written premium • Customers include 15% of the Fortune® 500 • Serving customers that retain significant risk through captives & large deductibles A P P E N D I X • Expertise in credit risk management • High barriers to entry • High customer retention • Casualty-oriented lines of coverage Premium Flows Product Mix Based on YE 2025 data Workers' Comp 42% Commercial Auto 34% General Liability 22% Property 2% Direct premium by Old Republic Ceded back to Customers15-20% Retained by Old Republic
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24 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Start-up Operating Companies Seven new operating companies focused on specialty niches. INLAND MARINE EXCESS & SURPLUS LAWYERS PROFESSIONAL ACCIDENT & HEALTH CYBER ENVIRONMENTAL PROPERTY Matt Bisig Ralph Sabbagh Mike Furlong Gary Nidds CJ Pruzinsky George Holderied Patrick Hagerty Launched 2021 Primarily E&S Launched 2021 Exclusively E&S Launched 2023 Admitted Launched 2023 Admitted Launched 2025 Primarily E&S Launched 2025 Primarily E&S Launched 2026 Primarily E&S Provides builders risk coverage for residential, commercial and institutional construction projects Inland marine coverage for contractors equipment Casualty and property risks individually underwritten Binding authority business though select distribution partners Exclusively through wholesale brokers Lawyers professional liability (LPL) coverage Small firms up to 35 attorneys Exclusive distribution relationships by state with affinity groups Employer Stop Loss coverage protects self-funded employers from catastrophic individual or unexpected aggregate medical claims Tailored to client needs and risk tolerance Cyber and tech E&O for mid sized and larger companies First-party protection and third-party liability protection Environmental liability coverages with a focus on providing specialized Monoline Pollution and blended-form General Liability and Pollution coverages Commercial property coverage for large, Fortune 1000 corporations with domestic and global exposures Capacity deployed on a quota-share basis with primary and/or excess attachments Decentralized operations | Proven start-up expertise | Common culture | Aligned compensation structures Leverage ORI’s financial strength | Differentiated by niche expertise and service A P P E N D I X
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25 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Centers of Excellence Driving operational excellence and reinforcing our culture across the organization. • Standardized best practices • Cross-group collaboration • Data-driven decision making • Innovation • Continuous improvement • Shared lessons learned CENTERS OF EXCELLENCE Human Resources IT/Security Accounting Legal Compliance Marketing Distribution Underwriting Risk Control Actuarial/Data Analytics Customer Care Center Claims Managed Care A P P E N D I X
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26 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. The Lodestar Embodies our Mission by Binding Organization, Purpose and Long-Term Strategy Into a Coordinated Whole A P P E N D I X Our People Our people's expertise and judgment power our ability to deliver dependable outcomes. Our Shareholders We manage capital with discipline to ensure strength and stability for the long run. Our Community We operate with integrity to earn trust within our industry and with the public. Our Customers We deliver specialized insurance solutions through enduring customer partnerships.
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27 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Old Republic’s Culture, Operating Philosophy, and Institutional Memory A P P E N D I X It starts with “we.” We support one another and have each other’s backs. We are efficient. We optimize for better outcomes and avoid over-engineering. We are humble. But we are confident. We are patient and thoughtful. We don’t panic or overreact. We are inclusive. We are collaborative and respect different points of view. We avoid bureaucracy. We empower decentralized decision making. We act with integrity. We are honest and trustworthy. We do things right. We compete with discipline and accountability. We are creative and innovative. We think outside the box. We communicate clearly. We are concise, direct, and consistent. We think long term. We don’t let short-term or quarterly results drive our decisions. We act with urgency. We move quickly, take ownership, and follow through. We strive for excellence. Our standards are high and we push ourselves to be better.
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28 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Non-GAAP Reconciliation Amounts in millions, except per share data Although Generally Accepted Accounting Principles (GAAP) uses net income as the measure of total profitability, management uses net operating income, a non-GAAP financial measure defined as net income excluding net investment gains (losses) and bargain purchase gain, in its evaluation of periodic and long-term results. Net operating income, however, does not replace GAAP net income as a measure of total profitability. A P P E N D I X Quarter Ended September 30, 2025 2026 $ 279.5 $ 243.2 82.7 (63.2) — 124.9 $ 196.7 $ 181.4 Quarter Ended September 30, 2025 2026 $ 1.11 $ 0.99 0.33 (0.25) — 0.51 $ 0.78 $ 0.73 Net income Net realized investment gains (losses) Gain on bargain purchase Net operating income Net income Net realized investment gains (losses) Gain on bargain purchase Net operating income Overall Results Attributable to Shareholders Per Diluted Share Attributable to Shareholders Nine Months Ended September 30, 2025 2026 $ 729.0 $ 895.6 121.3 232.5 — 124.9 $ 607.7 $ 538.1 Nine Months Ended September 30, 2025 2026 $ 2.91 $ 3.62 0.49 0.95 — 0.50 $ 2.42 $ 2.17
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29 ©2026 OLD REPUBLIC. ALL RIGHTS RESERVED. Forward-Looking Statements Some of the oral or written statements made in the Company's reports, press releases, and conference calls following earnings releases, can constitute "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995. These forward-looking statements generally include words such as "expect," "predict," "estimate," "will," "should," "anticipate," "believe," and similar expressions. Any such forward-looking statements involve assumptions, uncertainties, and risks that may affect the Company's future performance. Historical data pertaining to the operating results, liquidity, and other performance indicators applicable to an insurance enterprise such as Old Republic are not necessarily indicative of results to be achieved in succeeding years. In addition to the factors cited below, the long-term nature of the insurance business, seasonal and annual patterns in premium production and incidence of claims, changes in yields obtained on invested assets, changes in government policies and free markets affecting inflation rates and general economic conditions, and changes in legal precedents or the application of law affecting the settlement of disputed and other claims can have a bearing on period-to-period comparisons and future operating results. Old Republic's Specialty Insurance segment results can be affected by the level of market competition, which is typically a function of available capital and expected returns on such capital among competitors; general economic considerations, including the levels of investment yields, inflation rates, and the impacts of tariffs; periodic changes in claim frequency and severity patterns caused by natural disasters, weather conditions, accidents, illnesses, and work-related injuries; claims development and the impact on loss reserves; adequacy and availability of reinsurance; uncertainties in underwriting and pricing risks; and unanticipated external events. Old Republic’s Title Insurance segment results can be affected by similar factors, and by changes in national and regional housing demand and values, the availability and cost of mortgage loans, and employment trends. Life and accident insurance earnings can be affected by the levels of employment and consumer spending, changes in mortality and health trends, and alterations in policy lapsation rates. At the parent holding company level, operating earnings or losses are generally reflective of the amount of debt outstanding and its cost, interest income, the levels of investments held, and period-to-period variations in the costs of administering the Company's widespread operations. In addition, results could be particularly affected by technology and security breaches or failures, including cybersecurity incidents. A more detailed listing and discussion of the risks and other factors which affect the Company's risk-taking insurance business are included in Part I, Item 1A - Risk Factors, of the Company's 2025 Form 10-K, and the various risks, uncertainties, and other factors that are included from time to time in other Securities and Exchange Commission filings. Any forward-looking statements or commentaries speak only as of their dates. Old Republic undertakes no obligation to publicly update or revise any and all such comments, whether as a result of new information, future events or otherwise, and accordingly they may not be unduly relied upon. A P P E N D I X