Guidewire insider sells shares via Form 144

Guidewire Software reported multiple insider dispositions via a Form 144 filing, primarily sales of Common Stock.

Rhea-AI Filing Summary

Guidewire Software reported multiple insider dispositions via a Form 144 filing, primarily sales of Common Stock. The excerpt lists repeated open-market sales of 1,200 shares on several dates in Mar–Jun 2026 and a single larger disposition of 4,737 shares for $776,194.87. The filing also shows Restricted Stock Units acquired on 06/15/2026 and a listed quantity of 5,830 in the securities-to-be-sold field.

Insights

Insider Transactions Analyst

Frequent small share sales plus one larger disposition; timing appears concentrated in Mar–Jun 2026.

The filing lists numerous 1,200-share sales on dates including 03/23/2026 through 06/15/2026, and a single sale of 4,737 shares reported with an aggregate value of $776,194.87. The sequence is consistent with systematic dispositions rather than a single large block trade.

Cash‑flow treatment and whether trades were pursuant to a trading plan are not shown in the excerpt; subsequent filings or footnotes would be needed for that context.

Key Figures

Repeated sales per trade: 1,200 shares Larger reported disposition: 4,737 shares Aggregate value shown: $776,194.87 +1 more

4 metrics

Repeated sales per trade 1,200 shares Multiple open-market disposals between <date>Mar–Jun 2026</date>

Larger reported disposition 4,737 shares Single sale reported with aggregate proceeds

Aggregate value shown $776,194.87 Reported proceeds for the 4,737-share disposition

RSUs acquired 5,830 Restricted Stock Units acquired as compensation on <date>06/15/2026</date>

Key Terms

Form 144, Restricted Stock Units, Issuer

3 terms

Form 144 regulatory

"repeated header lines referencing the filing and sales records"

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.

Restricted Stock Units financial

"Acquired as compensation - Restricted Stock Units on 06/15/2026"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

Issuer regulatory

"Securities To Be Sold: Issuer listed next to RSU acquisition"

FAQ

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

The filing lists multiple open-market sales of Common Stock, including repeated 1,200-share transactions in Mar–Jun 2026 and a single sale of 4,737 shares reported with an aggregate value of $776,194.87.

Does the Form 144 show any acquisitions or awards for GWRE insiders?

Yes. The excerpt records Common Stock acquired as compensation via Restricted Stock Units on 06/15/2026 with a listed quantity of 5,830 under securities-to-be-sold, indicating recent compensation-related issuances.

How frequent were the disclosed GWRE insider sales?

Sales occurred frequently: the filing shows multiple consecutive weekly sales of 1,200 shares across April, May, and June 2026, indicating a pattern of recurring dispositions during that period.

What cash value is explicitly shown for any GWRE insider sale?

The excerpt shows one aggregate sale value of $776,194.87 tied to a disposition of 4,737 shares. Other per-trade dollar figures are included next to individual trade lines but no consolidated proceeds total is provided.

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

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Accepted by SEC EDGAR 06/16/2026 - 07:53 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 Pl Suite 200 San Mateo CALIFORNIA 94403
Phone	650-357-9100
Name of Person for Whose Account the Securities are To Be Sold	Michael George 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	CEO, 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 Stock	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 38th Floor New York NY 10004	5830	692271.72	83256364	06/16/2026	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	06/15/2026	Acquired as compensation - Restricted Stock Units	Issuer			5830	06/15/2026	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
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/15/2026	1200	148620
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/08/2026	1200	162744
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/01/2026	1200	190704
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	05/26/2026	1200	166212
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	05/18/2026	1200	153828
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	05/11/2026	1200	163656
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	05/04/2026	1200	170292
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	04/27/2026	1200	165708
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	04/20/2026	1200	167700
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	04/13/2026	1200	142524
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	04/06/2026	1200	181368
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	03/30/2026	1200	174888
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	03/23/2026	1200	186672
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	03/17/2026	4737	776194.87

144: Remarks and Signature

Remarks
Date of Notice	06/16/2026
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	By: Winston King, Attorney-in-Fact for Michael G. Rosenbaum
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)