Michael Rosenbaum plans $225K Guidewire stock sale

Guidewire Software, Inc. (GWRE) is the issuer for a Form 144 notice filed on behalf of Michael George Rosenbaum, covering planned sales of 1,200 shares of common stock through Morgan Stanley Smith Barney LLC under Rule 144.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) is the issuer for a Form 144 notice filed on behalf of Michael George Rosenbaum, covering planned sales of 1,200 shares of common stock through Morgan Stanley Smith Barney LLC under Rule 144. The shares relate to Performance Shares and are listed with an expected sale date of August 24, 2026.

The notice also lists prior Rule 144 sales of Guidewire common stock for Rosenbaum during the past three months, including multiple transactions of 1,200 shares each and one transaction of 5,830 shares on June 16, 2026, all reported with corresponding dollar amounts.

Key Figures

Shares proposed to be sold: 1,200 shares Approximate aggregate market value of proposed sale: $225,384.00 Largest single sale in past 3 months: 5,830 shares +3 more

6 metrics

Shares proposed to be sold 1,200 shares Guidewire common stock under current Rule 144 notice

Approximate aggregate market value of proposed sale $225,384.00 For proposed sale of 1,200 Guidewire common shares

Largest single sale in past 3 months 5,830 shares Guidewire common stock sold on June 16, 2026

Dollar amount for June 16, 2026 sale $692,271.69 Sale of 5,830 Guidewire common shares on June 16, 2026

Shares sold on August 17, 2026 1,200 shares Guidewire common stock sold by Michael George Rosenbaum

Dollar amount for August 17, 2026 sale $207,456.00 Sale of 1,200 Guidewire common shares on August 17, 2026

Key Terms

Rule 144, Performance Shares, Securities To Be Sold

3 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.

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.

Securities To Be Sold financial

"144: Securities To Be Sold Common | 09/15/2023"

FAQ

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

What does this Form 144 filing involve for Guidewire Software, Inc. (GWRE)?

The Form 144 relates to a planned sale of 1,200 shares of Guidewire Software, Inc. common stock by Michael George Rosenbaum under Rule 144, along with disclosure of several prior sales over the past three months.

How many GWRE shares are proposed to be sold under this Form 144?

The filing covers a proposed sale of 1,200 shares of Guidewire Software, Inc. common stock, listed as common stock received as Performance Shares and to be sold through Morgan Stanley Smith Barney LLC.

What is the approximate value of the GWRE shares in the proposed Form 144 sale?

The proposed sale of 1,200 Guidewire shares is shown with an approximate aggregate market value of $225,384.00, as part of the Rule 144 disclosure for the planned transaction.

When is the proposed sale date for the GWRE shares in this Form 144?

The proposed sale date listed for the 1,200 Guidewire common shares is August 24, 2026, with the shares expected to be sold on the NYSE through Morgan Stanley Smith Barney LLC.

What GWRE share sales by Michael George Rosenbaum occurred in the last three months?

The filing lists multiple sales of 1,200 shares of Guidewire common stock on various dates in June–August 2026 and one sale of 5,830 shares on June 16, 2026, each reported with corresponding dollar amounts.

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

The Form 144 covers common stock of Guidewire Software, Inc., identified as Performance Shares to be sold by Michael George Rosenbaum in compliance with Rule 144 requirements.

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

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Available on EDGAR 08/24/2026 - 04:05 PM EDT Accepted by SEC EDGAR 08/24/2026 - 04:05 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	225384.00	83256364	08/24/2026	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	08/17/2026	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
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/08/2026	1200	162744.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/01/2026	1200	190704.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/26/2026	1200	166212.00

144: Remarks and Signature

Remarks
Date of Notice	08/24/2026
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)