Guidewire insider plans $175K stock sale

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) has a notice filed under Rule 144 on behalf of Michael George Rosenbaum for the potential sale of 1,200 shares of common stock, held at Morgan Stanley Smith Barney LLC, with an aggregate market value of $175,044.00 and listed on the NYSE. The table indicates 81,992,669 shares outstanding of Guidewire common stock. The filing also lists prior Rule 144 sales by Rosenbaum over the past three months, including multiple 1,200‑share transactions and a larger sale of 5,830 shares on June 16, 2026.

Key Figures

Shares proposed to be sold: 1,200 shares Aggregate market value of proposed sale: $175,044.00 Shares outstanding: 81,992,669 shares +3 more

6 metrics

Shares proposed to be sold 1,200 shares Common stock to be sold under Rule 144 for Michael George Rosenbaum

Aggregate market value of proposed sale $175,044.00 Value associated with the 1,200 GWRE shares in the securities information table

Shares outstanding 81,992,669 shares Guidewire common stock shares outstanding as listed in the securities information section

Sale on September 8, 2026 1,200 shares for $192,624.00 Common stock sale by Michael George Rosenbaum in the past 3 months table

Sale on June 16, 2026 5,830 shares for $692,271.69 Larger common stock sale reported in the past 3 months section

Sale on June 22, 2026 1,200 shares for $126,804.00 Common stock sale listed among recent Rule 144 transactions

Key Terms

Rule 144, Performance Shares, aggregate market value, Securities To Be Sold

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.

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.

aggregate market value financial

"Common ... | 1200 | 175044.00 | 81992669"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

Securities To Be Sold regulatory

"144: Securities To Be Sold"

FAQ

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

What does the Form 144 filing disclose for Guidewire Software (GWRE)?

The Form 144 notice discloses that 1,200 shares of Guidewire Software, Inc. common stock may be sold under Rule 144 on behalf of Michael George Rosenbaum through Morgan Stanley Smith Barney LLC.

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

The filing states that 1,200 shares of Guidewire common stock are proposed to be sold, with an aggregate market value of $175,044.00 as reflected in the securities information table.

How many Guidewire Software (GWRE) shares are outstanding according to the filing?

The securities information section reports that there are 81,992,669 shares outstanding of Guidewire Software, Inc. common stock, providing context for the potential 1,200‑share sale under Rule 144.

What type of GWRE securities are being sold and how were they acquired?

The filing identifies the securities as common stock, categorized as Performance Shares, with the issuer listed as the source in the Securities To Be Sold section dated September 15, 2023.

What prior GWRE sales by this insider are reported in the last three months?

The filing lists multiple prior sales of 1,200 GWRE shares on various dates and one larger sale of 5,830 shares on June 16, 2026 for $692,271.69, all categorized as common stock sales by Michael George Rosenbaum.

On which market is Guidewire Software (GWRE) stock listed in this filing?

The securities information section identifies the exchange as the NYSE for the Guidewire Software, Inc. common stock referenced in the Rule 144 notice.

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

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Available on EDGAR 09/14/2026 - 04:43 PM Accepted by SEC EDGAR 09/14/2026 - 04:37 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	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	175044.00	81992669	09/14/2026	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	09/08/2026	1200	192624.00
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	09/14/2026
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)