Guidewire insider plans $193K stock sale

Guidewire Software, Inc. (GWRE) is the issuer of common stock for which Michael George Rosenbaum filed a Rule 144 notice to sell 1,200 shares, with an indicated value of $192,624.00, through Morgan Stanley Smith Barney LLC.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) is the issuer of common stock for which Michael George Rosenbaum filed a Rule 144 notice to sell 1,200 shares, with an indicated value of $192,624.00, through Morgan Stanley Smith Barney LLC. The notice lists these shares as performance shares acquired on September 15, 2023. It also reports multiple prior open-market sales of common stock over the past three months, including several 1,200‑share transactions and one 5,830‑share transaction, each with stated dollar proceeds.

Key Figures

Shares to be sold: 1,200 shares Indicated value of planned sale: $192,624.00 Performance Shares acquired: 1,200 shares +3 more

6 metrics

Shares to be sold 1,200 shares Guidewire common stock covered by the Rule 144 notice

Indicated value of planned sale $192,624.00 Value associated with 1,200 shares of Guidewire common stock

Performance Shares acquired 1,200 shares Performance Shares acquired on September 15, 2023

Sale on August 31, 2026 1,200 shares for $245,328.00 Reported prior sale of Guidewire common stock

Sale on June 16, 2026 5,830 shares for $692,271.69 Largest single sale reported in past three months

Sale on June 22, 2026 1,200 shares for $126,804.00 One of multiple 1,200‑share sales disclosed

Key Terms

Rule 144, Form 144, Performance Shares, person

4 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.

Form 144 regulatory

"144: Filer Information"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Performance Shares financial

"Common | 09/15/2023 | Performance Shares | ISSUER"

Performance shares are a type of company stock given to executives or employees that only become theirs if the company meets specific goals, like hitting certain profits or growth targets. They motivate leaders to work toward the company’s success, because their additional shares depend on achieving these results.

person regulatory

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

FAQ

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

What does the Form 144 filing for GWRE disclose about planned share sales?

The Form 144 notice discloses that 1,200 shares of Guidewire Software common stock may be sold under Rule 144, with an indicated value of $192,624.00, through Morgan Stanley Smith Barney LLC Executive Financial Services.

Who is selling GWRE shares in this Form 144 notice?

The notice is filed for the account of Michael George Rosenbaum, in connection with Guidewire Software, Inc. common stock, and is submitted through Morgan Stanley Smith Barney LLC Executive Financial Services as the brokerage firm.

What type of GWRE securities are covered by this Form 144?

The filing covers common stock of Guidewire Software, Inc. The 1,200 shares to be sold are identified as Performance Shares acquired on September 15, 2023 from the issuer.

What prior GWRE share sales are reported over the past three months?

The notice reports multiple prior sales of Guidewire common stock, including several 1,200‑share transactions and one 5,830‑share transaction, with stated proceeds such as $245,328.00 on August 31, 2026 and $692,271.69 on June 16, 2026.

Which broker is handling the GWRE shares in this Form 144?

The broker listed is Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004, in connection with the 1,200 Guidewire Software common shares subject to the Rule 144 notice.

What is the reported value of the GWRE shares to be sold under this notice?

The filing associates the planned sale of 1,200 Guidewire common shares with a value of $192,624.00, as part of the Rule 144 notice submitted on behalf of Michael George Rosenbaum.

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

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Available on EDGAR 09/08/2026 - 04:09 PM EDT Accepted by SEC EDGAR 09/08/2026 - 04:08 PM EDT 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	0001784996
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 Place, Suite 200 San Mateo CALIFORNIA 94403
Phone	(650) 357-9100
Name of Person for Whose Account the Securities are To Be Sold	MIKE ROSENBAUM
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	Officer
Relationship to Issuer	Director

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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	1200	192624.00	83256364	09/08/2026	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	09/15/2023	Performance Shares	ISSUER			1200	09/15/2023	Not Applicable

* 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
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/31/2026	1200	245328.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/24/2026	1200	225384.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/17/2026	1200	207456.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/10/2026	1200	203400.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/03/2026	1200	187104.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/27/2026	1200	170772.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/20/2026	1200	176904.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/13/2026	1200	166164.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/06/2026	1200	157956.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/29/2026	1200	149148.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/22/2026	1200	126804.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/16/2026	5830	692271.69
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/15/2026	1200	148620.00

144: Remarks and Signature

Remarks
Date of Notice	09/08/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	10/14/2025
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/ Michael George Rosenbaum
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)