Safety Insurance Group Director-Level Entities Report 38,835 Share Sale at $103.08

Joint Filing by Insurance Company Affiliates and Subsidiaries

The disclosure reveals a coordinated filing by two affiliated Massachusetts corporations: SRB Corporation and The Plymouth Rock Company Incorporated (PRC). SRB operates as a wholly-owned subsidiary of PRC and serves as an investment manager, which establishes its connection to the reported transaction. Both entities maintain director-level relationships with Safety Insurance Group Inc., the parent company of the NASDAQ-listed insurer. The joint filing structure was necessary because the reporting persons may be deemed a "group" under Section 13(d)(3) of the Securities Exchange Act of 1934, though each entity expressly disclaims beneficial ownership of securities held by the other.

The filing indicates that SRB disclaims beneficial ownership of the shares reported, emphasizing that its role as investment manager does not constitute beneficial ownership for purposes of Section 16 compliance. Similarly, PRC disclaims beneficial ownership except to the extent of its pecuniary interest in the reported shares. This distinction is significant for investors tracking insider transactions, as it clarifies the legal relationship between the reporting entities and the underlying ownership position. The disclaimer language suggests a structured arrangement typical of insurance company holding arrangements, where multiple subsidiaries and affiliated entities hold shares without individual beneficial ownership claims.

Subsidiary Network Holds Majority of Reported Position

The beneficial ownership structure involves an extensive network of subsidiaries and affiliated insurance entities. PRC directly holds 4,120 shares of Safety Insurance Group common stock. An additional 755,559 shares are held in aggregate by nine subsidiaries of PRC, including Plymouth Rock Security Corporation, Plymouth Rock Assurance Corporation, Plymouth Rock Assurance Preferred Corporation, Plymouth Rock Assurance Corporation of New York, Pilgrim Insurance Company, Plymouth Rock Home Assurance Corporation, and three Bunker Hill-branded insurance entities. This subsidiary structure reflects the complex corporate organization typical of regional insurance holding companies, where individual operating subsidiaries maintain separate licenses and capital structures.

Beyond the direct PRC subsidiary network, the filing discloses that Palisades Safety and Insurance Association (PSIA), a New Jersey reciprocal insurance exchange managed by a PRC subsidiary, and its affiliated entities hold an additional 954,060 shares in aggregate. This block includes stakes held by High Point Safety and Insurance Company, High Point Property and Casualty Insurance Company, High Point Preferred Insurance Company, Palisades Insurance Company, Twin Lights Insurance Company, and Teachers Auto Insurance Company of New Jersey. The total of 1,713,739 shares beneficially owned following the transaction represents the combined position across all these entities. Investors analyzing Safety Insurance Group's share structure should note that this substantial ownership block operates through a multi-layered subsidiary framework.

Transaction Execution and Pricing Details

The reported transaction involved the sale of 38,835 shares executed on July 24, 2026, at a per-share price of $103.0776. This transaction was classified as a sale (code "S") under Section 16 reporting protocols. The filing was submitted to the Securities and Exchange Commission on July 27, 2026, within the required two business day window for insider transaction reporting. No indication appears in the disclosure that this transaction was executed pursuant to a Rule 10b5-1 trading plan, which would have been noted if applicable.

The transaction reduced the combined beneficial ownership position held by the reporting persons and their affiliated entities from a higher level to the post-transaction amount of 1,713,739 shares. While the filing does not disclose the aggregate transaction value, applying the stated share count and price yields a calculable figure that investors may use in their analysis. The pricing level of approximately $103.08 per share provides market context for the transaction, though the filing contains no commentary from the reporting persons regarding timing, rationale, or market conditions influencing the sale decision.

Indirect Ownership Classification and Reporting Structure

The filing designates the post-transaction beneficial ownership as held indirectly (classified as "I" in the ownership form field) through the various subsidiary and affiliated entity structures described in the explanatory notes. This indirect classification is appropriate given that Safety Insurance Group shares are held by multiple subordinate entities rather than directly by SRB or PRC on an individual basis. The complexity of the holding structure necessitates detailed footnote explanations describing the corporate relationships and subsidiary networks involved in maintaining the beneficial ownership position.

The indentation and footnote structure of the filing reflects regulatory requirements for transparency when insider transactions occur through corporate entities rather than individuals. Each subsidiary layer and affiliated entity is identified by its legal name, state of incorporation, and relationship to the parent entities. For investors seeking to understand the true economic interest represented by this 1.7-million-plus share position, the filing provides the necessary roadmap through its detailed identification of all entities participating in the beneficial ownership arrangement. However, investors should note that the disclaimers of beneficial ownership by certain reporting persons may create complexity in assessing voting control and economic interest allocation across the subsidiary network.

Director Status and Regulatory Reporting Obligations

Both SRB Corporation and The Plymouth Rock Company Incorporated are identified in the filing as maintaining director-level relationships with Safety Insurance Group Inc. The checkbox marked for "Director" establishes their reporting obligations under Section 16(a) of the Securities Exchange Act of 1934. This regulatory classification requires the timely disclosure of changes in beneficial ownership and creates accountability for insider trading compliance. The filing signature of Frederick C. Childs on July 27, 2026, provides the required certification that the disclosed transaction information is accurate.

The director-level relationship subjects these affiliated entities to heightened scrutiny under securities law. Any subsequent transactions by these reporting persons in Safety Insurance Group shares would similarly require Form 4 disclosure within two business days of execution. Investors monitoring insider activity at Safety Insurance Group should track future filings from these affiliated entities, as their substantial ownership position and director-level status make their trading activity material to market analysis. The joint filing approach indicates that the reporting persons have coordinated their compliance obligations, suggesting ongoing coordination in their investment activities.

Massachusetts Corporate Base and Insurance Industry Focus

Both reporting entities are Massachusetts corporations with registered addresses at 695 Atlantic Avenue in Boston, reflecting the New England concentration of Safety Insurance Group's corporate structure and operations. The use of multiple state jurisdictions for subsidiary entities—including New York and New Jersey corporations within the holding structure—indicates a multi-state insurance operations footprint. Plymouth Rock-branded entities suggest this ownership structure is connected to the Plymouth Rock insurance organization, which historically has been associated with regional auto and property insurance operations in the northeastern United States.

The subsidiary names and jurisdictions reveal a diversified insurance portfolio spanning personal auto insurance, property insurance, preferred coverage lines, and reciprocal insurance exchange structures. The Bunker Hill-branded entities suggest either a historic acquisition or a separate operating brand within the corporate structure. The presence of state-specific entities in New York and New Jersey reflects the regulated nature of insurance operations, where each state typically requires separate licensed entities. This geographic and operational diversity within the beneficial ownership structure indicates that the shareholders represented by these reporting persons maintain substantial economic interests across multiple insurance product lines and geographic markets.

Pecuniary Interest and Ownership Disclaimers

The filing contains explicit language wherein PRC disclaims beneficial ownership of the reported shares except to the extent of its pecuniary interest. This qualified disclaimer is significant for understanding the nature of the beneficial ownership position. Under securities law, pecuniary interest refers to the economic benefit derived from share ownership, which may include dividend rights or proportional claims to corporate earnings. By limiting its beneficial ownership claim to the pecuniary interest, PRC may be declining to assert voting control or other non-economic attributes associated with share ownership.

SRB's disclaimer of beneficial ownership is more comprehensive, stating that it does not disclaim beneficial ownership based on its role as investment manager to PRC. This language protects SRB from being deemed a beneficial owner under Section 16 definitions while preserving its investment management function. For investors seeking to understand voting control and economic interest in Safety Insurance Group, these disclaimers suggest that the actual economic beneficiary may be PRC and its subsidiary structure rather than SRB as the investment manager. The complexity of these ownership arrangements reflects common practices in insurance holding company structures, where management entities and economic interest holders maintain separate legal and operational roles.

Form 4 Filing Standards and Compliance Timeline

The filing was executed in conformance with SEC Form 4 requirements under Section 16 of the Securities Exchange Act of 1934. The disclosure includes all required elements: identification of reporting persons, transaction date, securities description, transaction price, and post-transaction beneficial ownership. The filing was signed by Frederick C. Childs on July 27, 2026, and submitted to the Securities and Exchange Commission within the required two-business-day reporting window following the July 24, 2026, transaction execution date. The certification language on the form warns that intentional misstatements or omissions constitute federal criminal violations, establishing the legal weight behind the disclosure accuracy.

The standard Form 4 structure provides investors with consistent, comparable information across all insider transactions reported at NASDAQ-listed companies. The OMB approval number 3235-0287 and burden hour estimate of 0.5 hours per response reflect routine regulatory processing for standardized insider filings. While Form 4 disclosures are mandatory for reporting persons, investors should recognize that the filing provides transaction-level detail but typically does not include commentary on transaction rationale, market outlook, or future trading intentions from the reporting persons. The regulatory framework ensures transparency regarding who traded, what was traded, when the trade occurred, and at what price, but leaves interpretation of the transaction's significance to market participants and analysts.

Investment Structure and Beneficial Ownership Implications

The multi-layer subsidiary structure disclosed in this filing illustrates a common approach to holding insurance company shares through operating subsidiaries and affiliated entities. The 1,713,739 share position following the transaction represents a substantial stake in Safety Insurance Group. Without disclosure of the total outstanding shares, investors cannot calculate a precise ownership percentage from the filing alone. However, the size of the position and the extent of the subsidiary network indicate a significant long-term investment by the Plymouth Rock-affiliated entities in Safety Insurance Group shares.

The sale of 38,835 shares represents a modest reduction in an overall position measured in the millions of shares. This transaction may reflect routine portfolio management, rebalancing activities, or dividend reinvestment adjustments across the subsidiary network rather than a strategic shift in the overall beneficial ownership position. The transaction's modest size relative to the total position suggests the reporting persons maintain substantial confidence in Safety Insurance Group's equity value. Investors seeking to understand the significance of insider activity should evaluate individual transactions within the context of the reporting person's total holding, the frequency of recent transactions, and any public statements or guidance from company management regarding business performance and outlook.