Guidewire Software CAO & General Counsel Files Form 144 for Tax Withholding Sale

Summary of Proposed Transaction

On September 17, 2026, James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software, Inc., filed Form 144 indicating an intent to sell 11,814 shares of Common Stock through Morgan Stanley Smith Barney LLC, with an aggregate market value of approximately $1,706,784.36 (implying an approximate price of ~$144.47 per share).

Transaction Context & Plan Details

• Nature of Transaction: As detailed in the filing remarks, the planned sale consists of automatic sell-to-cover transactions to satisfy statutory tax withholding obligations resulting from the vesting of RSU and PSU awards on September 15, 2026.
• Acquisitions: The underlying shares vested from multiple RSU and PSU grants dating between September 2022 and September 2025, totaling 22,382 shares acquired across the tranches on September 15, 2026.
• Recent Prior Sales: The insider previously sold 1,684 shares on July 9, 2026, generating gross proceeds of $219,997.76.

Trading Significance

This filing carries Low trading significance. The transaction represents a non-discretionary, mandatory sell-to-cover to satisfy withholding tax liabilities associated with equity compensation vesting, rather than a discretionary divestment indicating management sentiment.