TRV · Travelers Companies, Inc. · Insider Trading

These are deferred common stock units received in lieu of cash compensation pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors. The deferred common stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Includes the deferred common stock units granted under one or more of the Company's directors' compensation plans. Also includes 1.564 deferred common stock units acquired on September 30, 2026 pursuant to the dividend reinvestment features of those plans, which will be distributed as described in footnote 1 above.

These are deferred common stock units received in lieu of cash compensation pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors. The deferred common stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Includes the deferred common stock units granted under one or more of the Company's directors' compensation plans. Also includes 44.05 deferred common stock units acquired on September 30, 2026 pursuant to the dividend reinvestment features of those plans, which will be distributed as described in footnote 1 above.

These are deferred common stock units received in lieu of cash compensation pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors. The deferred common stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Includes the deferred common stock units granted under one or more of the Company's directors' compensation plans. Also includes 19.634 deferred common stock units acquired on September 30, 2026 pursuant to the dividend reinvestment features of those plans, which will be distributed as described in footnote 1 above.

Represents the weighted average sales price for price increments ranging from $369.81 to $369.962. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price for all transactions reported on this Form 4.

Consists of deferred stock units awarded pursuant to the Company's Amended and Restated 2023 Stock Incentive Plan and the Deferred Compensation Plan for Non-Employee Directors. The deferred stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments beginning at least six months following termination of his or her service as a director pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Represents the weighted average sales price for price increments ranging from $367.86 to $368.84. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for increments ranging from $368.11 to $368.45. The Reporting Person undertakes to provide upon request by the Securities and Exchange Commission Staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for price increments ranging from $365.798 to $366.275. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for price increments ranging from $364.72 to $365.03. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for price increments ranging from $368.16 to $368.57. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

These are deferred common stock units received in lieu of cash compensation pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors. The deferred common stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Includes the deferred common stock units granted under one or more of the Company's directors' compensation plans. Also includes 46.885 deferred common stock units acquired on June 30, 2026 pursuant to the dividend reinvestment features of those plans, which will be distributed as described in footnote 1 above.

These are deferred common stock units received in lieu of cash compensation pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors. The deferred common stock units will be converted into shares of Company common stock on a one-for-one basis upon distribution. Distribution of shares of common stock occurs, at the election of the director, either in a lump sum or in annual installments pursuant to the Company's Deferred Compensation Plan for Non-Employee Directors.

Includes the deferred common stock units granted under one or more of the Company's directors' compensation plans. Also includes 20.595 deferred common stock units acquired on June 30, 2026 pursuant to the dividend reinvestment features of those plans, which will be distributed as described in footnote 1 above.

Represents the weighted average sales price for price increments ranging from $306.645 to $307.530. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for price increments ranging from $308.660 to $308.965. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Represents the weighted average sales price for price increments ranging from $307.650 to $308.645. The Reporting Person undertakes to provide, upon request by the Securities and Exchange Commission staff, the Issuer or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.