#1RLI INVESTOR PRESENTATION Quarter 1, 2023 RLI® DIFFERENT WORKS#2INTRODUCTION RLI® DIFFERENT WORKS#3STRATEGY From our niche product offerings to our business model, our culture to our results we're different. We will continue to: - RLI 3 Be a premier specialty underwriting company that achieves long-term industry leading combined ratios and book value growth. Seek out difficult markets while maintaining a highly diverse product portfolio. Remain a destination for talented, entrepreneurial underwriters with 'narrow & deep' expertise. Emphasize profit maximization and enhance our ability to grow over the long term, with a focus on organic opportunities and acquisitions that preserve the unique culture that has made RLI successful.#4FINANCIAL STRENGTH AND STABILITY Our financial track record has been stellar for decades - a testament to our culture and reputation as an excellent underwriting company. A+ SUPERIOR Financial Strength BEST A+ Superior A STRONG S&P Global WARD'S 50 TOP P&C PERFORMER FOR 32 YEARS 4.8/5 STARS ON glassdoor RLI 4#5SELECT MARKET INFORMATION RLI has a rich history as a publicly traded company and consistently creates value for its shareholders. Ticker/Exchange Share Price (as of 3/31/2023) RLI / NYSE $132.91 Annual Dividend Yield (as of 5/4/2023) $1.08 / 0.8% Market Cap $6.05 billion Annual Gross Premium (Trailing 4 qtr.) Employees 20 Year Annual Shareholder Return $1,621 million 987 17.0% RLI 5#66 THE RLI STORY RLI is a specialty insurance company with more than 50 years of experience serving diverse niche, property, casualty and surety markets. 1961 Founded contact lens insurance agency, Replacement Lens Inc. R 1961 1971 RLI common stock first traded on NASDAQ 1977 Began underwriting specialty P&C coverages in all 50 states 1996 Merged contact lens division with Hester Enterprises, maker of Maui Jim Sunglasses 2015 RLI Corp. 50th Anniversary 2020 25th consecutive year under 100 combined ratio RLI 50 YEARS E 1965 1965 RLI Corp. holding company formed 1970 | 1975 RLI becomes an Employee Stock Ownership Company 1975 1980 | 1976 First dividend paid to shareholders 1985 1990 Maxi gim 1995 | DOD 品中 1987 RLI common stock moved to NYSE 2000 2005 2004 Received upgraded AM Best rating to A+ (Superior) Financial Strength BEST A-Excellen | 2010 2011 Acquired Contractors Bonding and Insurance Co. | 2015 25 6= 2020 DIFFERENT WORKS 2023 2022 Sold minority ownership interest in Maui Jim, Inc. 2023 Increased regular dividend for 48 consecutive years#7DIVERSIFIED PRODUCT PORTFOLIO - NET PREMIUM Product diversification has fueled our growth & financial success. General Liability RLI 7 E&S Property SURPLUS LINES Excess Liability Personal Umbrella Earthquake PROPERTY (31%) CASUALTY (58%) Executive Products SURETY (11%) Marine Other Contract Commercial Miscellaneous Other Commercial Package Transportation Professional Services Trailing 4 Quarters Net Written Premium#8PRODUCT DISTRIBUTION Our strong customer relationships extend across a diverse distribution network. Retail agent/broker Wholesale Broker General liability General Agency / Carrier Partner CASUALTY PROPERTY Excess liability Personal umbrella Transportation Executive products Professional services Commercial package E&S property & Earthquake Marine Personal Lines SURETY Contract Commercial Miscellaneous RLI 8#9STRATEGY RLI® DIFFERENT WORKS#10RLI'S BUSINESS MODEL RLI is a domestic, specialty insurance company that does its own underwriting. • • • Underwriting Company Ownership Culture & Compensation Diversified Insurance Product Portfolio Growth by Design We hire experienced, entrepreneurial underwriters We focus on difficult markets that require unique expertise Strong feedback loop between underwriting and claims • Underwriting leadership compensation is tied to underwriting profit 91% Institutions & other public investors ■9% Insiders & Employee Stock Ownership Plan ("ESOP") • Our products are run like stand-alone businesses • Organic product growth • Diversification reduces corporate risk Many products are convenient and tailored to fill a void in the market • Talent acquisition & start-ups • Select balance sheet acquisitions RLI 10#11MARKET CYCLE MANAGEMENT RLI's strong people, products & processes allow us to effectively manage through any kind of market. INVEST in new people, products & processes in all markets Gross Premium ($ millions) $1,800 . EMPOWER underwriters to $1,600 capitalize to the fullest during $1,400 hard markets and pull back when necessary during soft markets $1,200 • ENFORCE strict underwriting $1,000 discipline throughout $800 MAXIMIZE financial strength & flexibility $600 $400 $200 RLI 11 $- 0 01 03 05 40 07 09 11 13 15 17 12 19 23 21 T4Q#12ENVIRONMENTAL, SOCIAL & GOVERNANCE PRINCIPLES We are committed to integrating sound Environmental, Social and Governance ("ESG") principles into our business, and our approach to sustainability reflects our focus on doing the right thing - for our customers, our employees, our communities and the environment. People Community We strive to create a diverse and inclusive environment where employees are supported, engaged, empowered and rewarded. We foster our ownership culture by providing competitive Total Rewards and offering diverse professional development, training, mentoring and educational opportunities. We are dedicated to supporting the communities in which we live and work. Through charitable gifts, educational scholarships, community service and volunteer programs, we're using our resources and talents to strengthen our communities and the nonprofit organizations that serve them. Environmental Stewardship We are committed to integrating sound environmental practices into our business to conserve natural resources and reduce our environmental footprint. Located on six and a half acres, RLI's 1.8-megawatt solar field produces annual electrical power equal to or exceeding the Company's annual electrical needs for its Corporate headquarters campus in Peoria, Illinois, which houses approximately 43 percent of our total workforce. Governance Our Board of Directors adheres to best practices in corporate governance to fulfill its responsibilities to shareholders and oversee management and the company's business results. We hold ourselves to high standards of ethical conduct and have a long history of strong corporate governance. For more information on our sustainability work visit: rlicorp.com/sustainability RLI® 12#13FINANCIAL RESULTS RLI® DIFFERENT WORKS#14MEASUREMENTS OF OUR SUCCESS Combined Ratio Book Value Growth (2) Operating Return on Equity (2) Capital Management Reserve Consistency 27 consecutive years under 100 combined ratio (1) 18.0% average annual growth in book value per share (including dividends) 12.1% average OROE 48 consecutive years of increased dividends (May 2023) $476 million reserve releases since 2018 12 margin (points) by which we beat the industry (2) RLI 14 $759 million amount returned to shareholders since 2018 (1) As of Year End 2022 (2) Over the last 10 years as of 12/31/22#15UNDERWRITING PROFIT RLI has achieved 27 straight years of a combined ratio below 100, and has beaten the industry ratio by an average of 12 points* over the last 10 years 120 110 100 90 80 70 70 60 60 1996 1997 RLI® 1998 1999 2000 2001 2002 (1) AM Best (2022). Aggregate & Averages - Property/Casualty, United States & Canada. 1996-2021 15 (2) Conning (2022). Property-Casualty Forecast & Analysis: By Line of Insurance, Fourth Quarter 2022. Estimated for the year ended December 31, 2022. 2003 2004 2005 2006 2007 RLI 2008 2009 2010 Industry(1)(2) 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 *Statutory basis as of year-end 2022#16OPERATING RETURN ON EQUITY 1 Over the previous 10 full years, RLI has averaged a 12.9% operating return on equity including Maui Jim earnings and a 12.1% operating return on equity exclusive of Maui Jim earnings. Inclusive of Maui Jim earnings Exclusive of Maui Jim earnings 13.5%³ 13.0% 13.0% 12.5% 11.9% 11.3% 10.6% 10.9% 14.7% 12.7%² 13.2% 12.1% 12.3% 10.8% 11.3% 10.5% 9.9% 9.8% 2013 2014 2015 2016 2017 2018 2019 2020 2021 18.9% 17.9% 18.9% 17.9% 20224 Q1 235 Operating earnings is a non-GAAP financial measure and consists of our GAAP net earnings adjusted by net realized gains/(losses), net unrealized gains/(losses) on equity securities that are recognized through net earnings in 2018 and forward and taxes related thereto. Net earnings is the most directly comparable financial measure to operating earnings. See our quarterly earnings releases for a reconciliation of net earnings to operating earnings. 2Solid bars represent operating ROE associated with RLI's core insurance operations and exclude RLI's non-core investee earnings from Maui Jim, which was sold in 2022. 3 Solid bars plus shaded areas represent operating ROE as reported in prior periods and include investee earnings from Maui Jim. Earnings from Maui Jim were negligible in 2022. STrailing 12 months. RLI 16#17DIVIDEND GROWTH RLI has a distinguished track record of success: 48 straight years of dividend increases* and a 5% growth rate over the last 10 years. SPECIAL DIVIDENDS $3.50/share Dec 2010 $2.50/share Dec 2011 $2.50/share Dec 2012 $1.50/share Dec 2013 $3.00/share Dec 2014 $2.00/share Dec 2015 $2.00/share Dec 2016 $1.75/share Dec 2017 $1.00/share Dec 2018 $1.00/share Dec 2019 $1.00/share Dec 2020 $2.00/share Dec 2021 $7.00/share Dec 2022 1.08 1.03 0.99 0.95 0.91 0.87 0.83 0.79 0.75 0.71 0.67 0.63 0.60 0.58 0.54 0.50 0.44 0.38 0.32 0.20 0.26 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 RLI® 17 2017 2018 2019 2020 2021 2022 Run Rate *As of May 2023#18INVESTMENT PORTFOLIO Investing for the long term: A diversified, highly-rated bond portfolio complemented by active and passive equities. TARGET ASSET ALLOCATION 80% BONDS PORTFOLIO ALLOCATION (as of 3/31/2023) Other Invested Assets 1.9% Agency 2.2% Equities 15.1% 20% Cash 4.1% EQUITIES BONDS: AA-quality; 4.4 duration EQUITIES: ETFs and active large-cap; dividend yield of 2.2% Emphasis on consistency of income and low turnover, not market timing RLI 18 Municipal 16.0% $3.42 Billion Investment Portfolio Corporate 31.6% Govt 11.4% ABS/CMBS 7.2% Mortgage Backed 10.5%#19TOTAL SHAREHOLDER RETURN Shareholder returns validate the RLI story. $2,500 S&P S&P P&C RLI 500 Index $2,000 1 year 27.8% -7.8% 0.4% year 19.6% 11.2% 11.2% $1,500 10 year 18.8% 12.2% 13.8% 20 year 17.0% 10.4% 10.4% $1,000 through 3.31.23 $500 $0 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Q1 23 ⚫RLI S&P 500 RLI 19#20THE FUTURE RLI® DIFFERENT WORKS#21VALUE CREATION OPPORTUNITIES RLI is pursuing multiple initiatives designed to create value. Cycle management Maximize margins throughout the cycle, organic growth enriched by market conditions Platform enhancements Investing in technology to leverage distribution and increase efficiency Talent acquisition Growth supported by hiring the best underwriters into the RLI model Acquisitions of niche P&C companies Capitalize on opportunities in niche spaces RLI 21#22COMPETITIVE ADVANTAGES RLI will capitalize on its competitive advantages to drive profitable growth. Capital strength Underwriting expertise Leverageable infrastructure Ownership mentality & aligned compensation Product & distribution diversification to support existing and new product growth RLI 22 22 A reputation for excellence among customers built over many years A track record that attracts opportunity - 'nothing succeeds like success'#23SELECTED FINANCIAL DATA (Amounts in millions) OPERATING RESULTS 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Q1 23 Gross premiums written 843.2 863.8 853.6 874.9 885.3 983.2 1,065.0 1,136.4 1,347.4 1,565.5 415.0 Consolidated revenue 705.6 775.2 794.6 816.3 797.2 818.1 1,003.6 983.6 1,179.2 1,698.0 364.9 Net earnings 126.3 135.4 137.5 114.9 105.0 64.2 191.6 157.1 279.4 583.4 98.8 Comprehensive earnings (loss) 119.1 170.8 89.9 113.8 140.3 30.2 258.7 213.3 220.5 304.5 136.5 FINANCIAL CONDITION 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Q1 23 Total investments 1,922.1 1,964.3 1,951.5 2,021.8 2,140.8 2,194.2 2,560.4 2,837.1 3,163.0 3,272.3 3,424.0 Total assets 2,738.9 2,774.3 2,735.5 2,777.6 2,947.2 3,105.1 3,545.7 3,938.5 4,508.3 4,767.1 4,836.2 Unpaid losses and 1,129.4 1,121.0 1,103.8 1,139.3 1,271.5 1,461.3 1,574.4 1,750.0 2,043.6 2,315.6 2,286.1 settlement expenses Total debt 148.2 148.4 148.6 148.7 148.9 149.1 149.3 149.5 199.7 199.9 199.9 Total shareholders' equity 829.0 845.1 823.5 823.6 853.6 806.8 995.4 1,136.0 1,229.4 1,177.3 1,303.9 Statutory surplus 859.2 849.3 865.3 860.0 864.6 829.8 1,029.7 1,121.6 1,240.6 1,437.3 1,488.7 RLI® 23#24SELECTED FINANCIAL DATA (Amounts in thousands, except per share data) SHARE INFORMATION 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Q1 23 Net earnings per share: Diluted 2.90 3.09 3.12 2.59 2.36 1.43 4.23 3.46 6.11 12.74 2.15 Comprehensive earning (losses) 2.74 3.90 2.04 2.56 3.15 0.67 5.72 4.70 4.82 6.65 2.97 per share: Diluted Cash dividends declared per 0.67 0.71 0.75 0.79 0.83 0.87 0.91 0.95 0.99 1.03 0.26 share: Ordinary Special 1.50 3.00 2.00 2.00 1.75 1.00 1.00 1.00 2.00 7.00 Book value per share 19.29 19.61 18.91 18.74 19.33 18.13 22.18 25.16 27.14 25.89 28.62 Closing stock price 48.69 49.40 61.75 63.13 60.66 68.99 90.02 104.15 112.10 131.27 132.91 Stock split 200% Weighted average shares 43,514 43,819 44,131 44,432 44,500 44,835 45,257 45,376 outstanding: Diluted 45,712 45,794 46,035 Common shares outstanding 42,982 43,103 43,544 43,945 44,148 44,504 44,869 45,143 45,289 45,470 45,555 OTHER FINANCIAL INFORMATION 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Q1 23 Net premiums written (T4Q) 78% 83% 83% 86% 87% 99% 84% 80% 85% 86% 87% to statutory surplus GAAP combined ratio 83.1 84.5 84.5 89.5 96.4 94.7 91.9 92.0 86.8 84.4 77.9 RLI® 24 *All share info adjusted for Jan 2014 2-for-1 stock split#25RLI DIF FER ENT WORKS RLICORP.COM