Guidewire GC plans tax-cover stock sales for 2026 vest

Guidewire Software, Inc. (GWRE) received a Form 144 notice from its Chief Administrative Officer and General Counsel, James Winston King, covering potential sales of common stock in connection with equity awards vesting on September 15, 2026.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) received a Form 144 notice from its Chief Administrative Officer and General Counsel, James Winston King, covering potential sales of common stock in connection with equity awards vesting on September 15, 2026. The notice lists planned sales of shares from multiple RSU and PSU vests, with transactions characterized as automatic sell-to-cover events to satisfy tax withholding obligations under the company’s Amended and Restated 2020 Stock Plan. The filing also notes a prior sale of common stock during the past three months.

Key Figures

RSU shares vesting (09/15/2022 grant): 861 shares PSU shares vesting (09/13/2023 grant): 19,701 shares Additional RSU shares vesting (09/13/2023 grant): 905 shares +5 more

8 metrics

RSU shares vesting (09/15/2022 grant) 861 shares Common stock from RSU vesting on September 15, 2026, acquired as compensation

PSU shares vesting (09/13/2023 grant) 19,701 shares Common stock from PSU vesting on September 15, 2026, acquired as compensation

Additional RSU shares vesting (09/13/2023 grant) 905 shares Common stock from RSU vesting on September 15, 2026, acquired as compensation

RSU shares vesting (09/11/2024 grant) 560 shares Common stock from RSU vesting on September 15, 2026, acquired as compensation

RSU shares vesting (09/11/2025 grant) 355 shares Common stock from RSU vesting on September 15, 2026, acquired as compensation

Shares sold in past 3 months 1,684 shares Guidewire common stock sold on July 9, 2026 by James Winston King

Proceeds from July 9, 2026 sale $219,997.76 Aggregate proceeds from sale of 1,684 shares of common stock

Notice date September 17, 2026 Date of Form 144 notice signed by James Winston King

Key Terms

Rule 144, sell-to-cover, restricted stock unit, performance stock unit, +1 more

5 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

sell-to-cover financial

"reflect automatic sell-to-cover transactions to satisfy tax withholding obligations"

Sell-to-cover is when part of newly issued or exercised company stock is immediately sold to pay required taxes and fees, so the recipient keeps the remaining shares. For investors this matters because it reduces the number of shares insiders or employees actually hold after a grant, can create small, routine share sales that aren’t signal of cashing out, and slightly increases share supply on the market—like selling a portion of a paycheck to cover the tax bill.

restricted stock unit financial

"Vesting of RSU (Grant Date: 09/15/2022)"

A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.

performance stock unit financial

"Vesting of PSU (Grant Date: 09/13/2023)"

A performance stock unit is a type of reward companies give to employees, usually managers, that depends on how well the company performs over time. If the company hits specific goals, the employee earns shares of stock, like earning a prize for reaching certain levels in a game. It motivates employees to work hard because their rewards are tied to the company's success.

Amended and Restated 2020 Stock Plan financial

"under the Issuer's Amended and Restated 2020 Stock Plan"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does Guidewire Software (GWRE) disclose in this Form 144?

The filing states that Chief Administrative Officer and General Counsel James Winston King has notified of planned sales of Guidewire common stock under Rule 144 in connection with equity awards vesting on September 15, 2026, primarily to cover tax withholding obligations.

How many Guidewire (GWRE) shares are tied to the September 15, 2026 RSU vests?

The notice lists RSU-related Guidewire common stock amounts of 861 shares (grant date September 15, 2022), 905 shares (grant date September 13, 2023), 560 shares (grant date September 11, 2024), and 355 shares (grant date September 11, 2025), all vesting on September 15, 2026.

How many Guidewire (GWRE) shares are from PSU vesting in this Form 144?

The filing includes a performance stock unit (PSU) vest with 19,701 shares of Guidewire common stock, from an award granted on September 13, 2023, scheduled to vest on September 15, 2026 and reported as acquired as compensation.

What prior Guidewire (GWRE) stock sales by James Winston King are disclosed?

The document reports that James Winston King sold 1,684 shares of Guidewire common stock on July 9, 2026 for aggregate proceeds of $219,997.76 during the past three months covered by the Form 144 disclosure.

How does the Form 144 describe the nature of the planned Guidewire (GWRE) sales?

The remarks state that the listed “Number of Shares to be Sold” reflects automatic sell-to-cover transactions to satisfy tax withholding obligations under Guidewire’s Amended and Restated 2020 Stock Plan, representing a portion of the RSU and PSU vests on September 15, 2026.

Which broker is identified for the potential Guidewire (GWRE) stock sales?

The notice identifies Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, as the broker for the Guidewire common stock covered under this Form 144 filing.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/17/2026 - 06:48 PM Accepted by SEC EDGAR 09/17/2026 - 06:48 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001586253
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Guidewire Software, Inc.
SEC File Number	001-35394
Address of Issuer	970 Park Pl, Suite 200 San Mateo CALIFORNIA 90803
Phone	650-357-9100
Name of Person for Whose Account the Securities are To Be Sold	James Winston King
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Chief Administrative Officer and General Counsel

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common Stock	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 38th Floor New York NY 10004	11814	1706784.36	81992669	09/17/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	09/15/2026	Vesting of RSU (Grant Date: 09/15/2022)	Issuer			861	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of PSU (Grant Date: 09/13/2023)	Issuer			19701	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/13/2023)	Issuer			905	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/11/2024)	Issuer			560	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/11/2025)	Issuer			355	09/15/2026	N/A (acquired as compensation)

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/09/2026	1684	219997.76

144: Remarks and Signature

Remarks	The amounts listed under 'Number of Shares to be Sold' reflect automatic sell-to-cover transactions to satisfy tax withholding obligations under the Issuer's Amended and Restated 2020 Stock Plan, representing a portion of the full RSU and PSU vests on September 15, 2026.
Date of Notice	09/17/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ James Winston King
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)