Business Description

We are a leading provider of private passenger automobile, commercial automobile, and homeowners insurance in Massachusetts. In addition to these coverages, we offer a portfolio of other insurance products, including dwelling fire, umbrella and business owner policies. Operating exclusively in Massachusetts, New Hampshire and Maine through our insurance company subsidiaries, Safety Insurance Company ("Safety Insurance"), Safety Indemnity Insurance Company ("Safety Indemnity"), Safety Property and Casualty Insurance Company ("Safety P&C"), and Safety Northeast Insurance Company (“Safety Northeast”) (together referred to as the "Insurance Subsidiaries"), we have established strong relationships with independent insurance agents, who numbered 797 in 1,063 locations throughout these three states during 2025. We have used these relationships and, in particular, our extensive knowledge of the Massachusetts market to become the fourth largest private passenger automobile carrier and the largest commercial automobile carrier in Massachusetts, capturing an approximate 9.4% and 13.0% share, respectively, of the Massachusetts private passenger and commercial automobile markets in 2025 according to statistics compiled by Commonwealth Automobile Reinsurers ("CAR"). We also are the third largest homeowners insurance carrier in Massachusetts with a 7.0% share of that market in 2024. We were ranked the 52 nd largest automobile writer in the country according to S&P Global Market Intelligence, based on 2024 direct written premiums. We were incorporated under the laws of Delaware in 2001, but through our predecessors, we have underwritten insurance in Massachusetts since 1979. Our Insurance Subsidiaries began writing insurance in New Hampshire during 2008 and Maine in 2016. The table below shows the amount of direct written premiums written in each state during the year ended December 31, 2025, 2024, and 2023. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Years Ended December 31, Direct Written Premiums 2025 ​ 2024 ​ 2023 Massachusetts $ 1,204,809 ​ $ 1,130,254 ​ $ 941,721 New Hampshire ​ 57,666 ​ ​ 52,095 ​ ​ 42,762 Maine ​ 16,130 ​ ​ 10,708 ​ ​ 6,741 Total $ 1,278,605 ​ $ 1,193,057 ​ $ 991,224 Website Access to Information The Internet address for our website is www.SafetyInsurance.com . All of our press releases and United States Securities and Exchange Commission ("SEC") reports are available for viewing or download at our website. These documents are made available as soon as reasonably practicable after each press release is made and SEC report is filed with, or furnished to, the SEC. Copies of any current public information about our Company is available without charge upon written, telephone, faxed or e-mailed request to the Office of Investor Relations, Safety Insurance Group, Inc., 20 Custom House Street, Boston, MA 02110, Tel: 877-951-2522, Fax: 617-603-4837, or e-mail: [email protected] . The materials on our website are not part of this report on Form 10-K nor are they incorporated by reference into this report and the URL above is intended to be an inactive textual reference only. The SEC maintains a website at www.sec.gov that contains reports, proxy and information statements and other information regarding issuers that file electronically with the SEC. 1 Table of Contents Our Competitive Strengths We Have Strong Relationships with Independent Agents. In 2025, independent agents accounted for approximately 68.8% of the Massachusetts personal lines insurance market measured by direct written premiums as compared to approximately 39.0% nationwide, based on data made available by Independent Insurance Agents and Brokers of America, Inc. and CAR. For that reason, our strategy is centered around, and we sell exclusively through, a network of independent agents. In order to support our independent agents and enhance our relationships with them, we: ● provide our agents with a portfolio of property and casualty insurance products at competitive prices to help them effectively address the insurance needs of their clients; ● provide our agents with a variety of technological resources which enable us to deliver superior service and support to them; and ● offer our agents competitive commission schedules and profit sharing programs.…