GWRE · Guidewire Software, Inc. · Insider Trading

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on January 13, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on April 9, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on April 9, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $142.2550 to $143.1700 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $141.2500 to $142.2150 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $140.2100 to $141.1950 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $143.5000 to $144.0000 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4695 to $144.4714 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4716 to $144.4719 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4714 to $144.4725 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4716 to $144.4719 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4713 to $144.4723 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

These Performance Shares cliff vested at the end of the three-year performance period based on the average performance of the three one-year performance periods. On September 9, 2026, the Compensation Committee determined that 136% of the performance conditions were met, resulting in an increase of 1,152 PSUs earned by the Reporting Person. On September 15, 2026, the time-based vesting was met.

These Performance Shares cliff vested at the end of the three-year performance period based on the average performance of the three one-year performance periods. On September 9, 2026, the Compensation Committee determined that 236% of the performance conditions were met, resulting in an increase of 43,342 PSUs earned by the Reporting Person. On September 15, 2026, the time-based vesting was met.

These Performance Shares cliff vested at the end of the three-year performance period based on the average performance of the three one-year performance periods. On September 9, 2026, the Compensation Committee determined that 136% of the performance conditions were met, resulting in an increase of 5,215 PSUs earned by the Reporting Person. On September 15, 2026, the time-based vesting was met.

These Performance Shares cliff vested at the end of the three-year performance period based on the average performance of the three one-year performance periods. On September 9, 2026, the Compensation Committee determined that 136% of the performance conditions were met, resulting in an increase of 10,013 PSUs earned by the Reporting Person. On September 15, 2026, the time-based vesting was met.

These Performance Shares cliff vested at the end of the three-year performance period based on the average performance of the three one-year performance periods. On September 9, 2026, the Compensation Committee determined that 236% of the performance conditions were met, resulting in an increase of 70,924 PSUs earned by the Reporting Person. On September 15, 2026, the time-based vesting was met.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

1. These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 10, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended January 13, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended January 13, 2026.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

These restricted stock units were granted on August 12, 2026, and are scheduled to become 100% vested after the earlier of one year from the grant date or Issuer's next annual meeting of stockholders.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.