Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 20 Custom House Street, Boston, Massachusetts 02110 (Address of principal executive offices including zip code) FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SEC ...

Exhibit 99.1 SAFETY INSURANCE GROUP, INC. ANNOUNCES SECOND QUARTER 2025 RESULTS AND RAISES THIRD QUARTER 2025 DIVIDEND Boston, Massachusetts, August 6, 2025. Safety Insurance Group, Inc. (NASDAQ:SAFT) ("Safety" or the "Company") today reported second quarter 2025 results. George M. Murphy, Chairman of the Board of Directors, President and Chief Executive Officer, commented: "For the quarter ended June 30, 2025, our combined ratio improved to 98.1% compared to 99.9% in the same period in the prior year. The ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from ______to ______ Commission File Number: 000-50070 SAFETY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 13-41816 ...

Exhibit 99.1 SAFETY INSURANCE GROUP, INC. ANNOUNCES FIRST QUARTER 2025 RESULTS AND DECLARES SECOND QUARTER 2025 DIVIDEND Boston, Massachusetts, May 7, 2025. Safety Insurance Group, Inc. (NASDAQ:SAFT) ("the Company" or "Safety") today reported first quarter 2025 results. George M. Murphy, Chairman of the Board of Directors, President and Chief Executive Officer, commented: "Safety's first quarter combined ratio in 2025 improved to 99.4% compared to 101.9% in the first quarter of 2024. The year-over-year chan ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 Or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 000-50070 SAFETY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 13-4181699 (State or other ...

Boston, Massachusetts, February 25, 2025. Safety Insurance Group, Inc. (NASDAQ:SAFT) ("Safety" or the "Company") today reported fourth quarter and year ended 2024 results. George M. Murphy, Chairman of the Board of Directors, President and Chief Executive Officer, commented: "For the year ended December 31, 2024, Safety Insurance continued to achieve significant direct written premium growth, which increased 20.4% over the prior year, driving our top-line revenue above $1 billion dollars for the first time ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from ______to ______ Commission File Number: 000-50070 SAFETY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 13-41816 ...

Insurance Operations - The company operates as the third largest private passenger auto premium insurance carrier, the second largest commercial auto insurance carrier, and the third largest homeowner insurance carrier in Massachusetts[20]. - Direct written premiums for private passenger automobile insurance increased to $543,167, representing 54.7% of total premiums in 2023, up from $427,665 (52.0%) in 2022[26]. - The company achieved a total of $991,224 in direct written premiums for all product lines in 2023, compared to $823,318 in 2022, reflecting a significant growth[26]. - The commercial automobile insurance segment accounted for $157,101 in direct written premiums, or 15.9% of total premiums in 2023, up from $143,571 (17.4%) in 2022[26]. - Homeowners insurance premiums reached $242,346, making up 24.5% of total premiums in 2023, compared to $208,577 (25.3%) in 2022[26]. - The company plans to further penetrate the Massachusetts, New Hampshire, and Maine markets across all lines of business[27]. - In 2023, 64.5% of private passenger automobile exposures insured had an other than private passenger policy with the company, compared to 65.2% in 2022[48]. - The company distributes products exclusively through independent agents, with 97.1% of direct written premiums for automobile insurance obtained through voluntary agents in 2023[42]. Technology and Innovation - The company is focused on expanding technology to enhance the ease of doing business for independent agents, thereby strengthening relationships[27]. - The company introduced the Safety Commercial Express system in 2021, which was updated in 2022 to allow for agent processing of endorsements[69]. - The Innovation Lab conducted significant research on Generative AI in 2023, with results expected in 2024[71]. - The automated adjuster assignment system categorizes new claims by severity, improving claims management efficiency[73]. - The company has made substantial investments in information technology to enhance agent support and customer service[53]. - The company’s proprietary software applications facilitate real-time policy issuance and data imports from major agency management systems[60]. - The company’s cybersecurity strategy includes ongoing employee education and monitoring for emerging threats[70]. Financial Performance - The bad debt expense as a percentage of direct written premiums was 0.2% in 2023, compared to 0.1% in 2022[76]. - The total incurred losses and LAE for the year 2023 amounted to $642,302, compared to $491,979 in 2022, reflecting a significant increase[97]. - The company paid total losses and LAE of $608,048 in 2023, compared to $515,759 in 2022, showing an increase in claims payments[97]. - The cumulative amounts paid for claims one year later were $198,414 for 2023, indicating the company's ongoing claims management[99]. - The company decreased loss reserves related to prior years by $47,381 in 2023, $57,279 in 2022, and $53,673 in 2021, indicating a trend of releasing redundant reserves[100]. - The reserves for losses and LAE at the end of 2023 were $603,081, up from $549,598 at the end of 2022[99]. - Management believes that the provision for unpaid losses and LAE as of December 31, 2023, is adequate to cover the ultimate cost of losses and claims incurred[93]. Reinsurance Strategy - The company’s reinsurance strategy involves selective partnerships with financially stable reinsurers, most of which have an A.M. Best rating of "A+" or "A"[104]. - In 2023, the company purchased three layers of excess catastrophe reinsurance providing $590,000 of coverage for property losses in excess of $75,000 up to a maximum of $665,000[105]. - For 2024, the company has increased its reinsurance coverage to $615,000 for property losses in excess of $75,000 up to a maximum of $690,000[106]. Investment Portfolio - As of December 31, 2023, the company's investment portfolio was valued at $1,424,113, with 73.9% in fixed maturity securities[133]. - The company has a high-quality investment portfolio primarily consisting of investment grade corporate fixed maturity securities, U.S. government and agency securities, and asset-backed securities[130]. - The estimated fair value of U.S. Treasury securities and obligations of U.S. Government agencies was $247,237 million, representing 23.5% of the total portfolio[141]. - Total estimated fair value of fixed income securities was $1,052,145 million as of December 31, 2023, slightly up from $1,050,155 million in 2022[141]. - The portfolio of fixed maturity investments included 65.8% rated Category 1 and 18.8% rated Category 2 as of December 31, 2023[143]. - The company has a commitment to inclusiveness and actively seeks highly-qualified candidates from diverse backgrounds[120]. Employee and Management Information - The company employs 539 employees as of December 31, 2023, all located in the New England region[119]. - George M. Murphy has been with the Company for over 35 years and was elected Chairman of the Board on May 17, 2023[172]. - Christopher T. Whitford has served as Chief Financial Officer since March 2, 2020, and has over 11 years of experience with the Company[173]. - James D. Berry has been employed by the Company for over 41 years and has directed the Massachusetts Private Passenger line of business since 2001[176]. - Ann M. McKeown, Vice President of Insurance Operations, will retire effective March 1, 2024, after over 34 years with the Company[178]. - Brian S. Lam was appointed Vice President of Insurance Operations effective March 1, 2024, and has been with the Company since 2002[182]. - The Company has adopted a Code of Business Conduct and Ethics applicable to all employees and directors, available on its website[192]. Regulatory and Risk Management - The company is subject to comprehensive regulation by state insurance departments, with the most recent financial condition examination covering the five-year period ending December 31, 2018[152]. - The Company completed its Own Risk Solvency Assessment (ORSA) filing for the 2023 period, as required by the National Association of Insurance Commissioners[169]. - The Company has significant exposure to market risk primarily due to changes in interest rates, with fixed and variable rate debt as sources of financing[405]. - The Company holds a substantial amount of fixed maturity investments, including U.S. and foreign government bonds, which are sensitive to interest rate changes[406]. - The company does not plan to enter into any derivative financial instruments for trading or speculative purposes[405]. Financial Metrics - Total assets increased to $2,094,004 as of December 31, 2023, up from $1,972,569 in 2022, reflecting a growth of approximately 6.2%[430]. - Loss and loss adjustment expense reserves rose to $603,081 in 2023, compared to $549,598 in 2022, indicating an increase of about 9.7%[430]. - The company's total investments reached $1,424,113 as of December 31, 2023, compared to $1,403,160 in 2022, marking a growth of approximately 1.5%[430]. - Cash and cash equivalents increased to $38,152 in 2023 from $25,300 in 2022, representing a significant increase of about 50.9%[430]. - The allowance for expected credit losses for fixed maturities increased from $678 in 2022 to $1,208 in 2023, reflecting a rise of approximately 78.1%[430]. - Shareholders' equity decreased to $804,267 in 2023 from $811,999 in 2022, a decline of about 0.9%[430]. - Net investment income increased to $56,377 million in 2023, up 20.3% from $46,725 million in 2022[138]. - Net effective yield improved to 4.0% in 2023, compared to 3.2% in 2022, reflecting a 25% increase[138].

Exhibit 99.1 SAFETY INSURANCE GROUP, INC. ANNOUNCES FOURTH QUARTER AND YEAR ENDED 2023 RESULTS Boston, Massachusetts, February 27, 2024. Safety Insurance Group, Inc. (NASDAQ:SAFT) ("Safety" or the "Company") today reported fourth quarter and year ended 2023 results. George M. Murphy, Chairman of the Board of Directors, President and Chief Executive Officer, commented: "2023 saw Safety Insurance post record top-line growth as Direct Written Premiums increased by 20.4% as a result of a 10.2% increase in overa ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q Commission File Number: 000-50070 SAFETY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 13-4181699 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 20 Custom House Street, Boston, Massachusetts 02110 (Address of principal executive offices including zip code) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECU ...