[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Guidewire Software, Inc. (GWRE) reporting a proposed sale of common stock by an insider. The notice lists 30,317 shares to be sold through Morgan Stanley Smith Barney at an aggregate market value of $7,362,964.57, with an approximate sale date of 09/16/2025 on the NYSE. The securities were acquired as restricted stock units on 09/15/2025 as compensation and are being sold by Michael George Rosenbaum's account via Guidewire Software address. The filing also discloses prior insider sales in the past three months totaling 25,525 shares across multiple dates and transactions, with gross proceeds reported for each sale.

Positive

• Rule 144 notice filed in compliance with specified broker and transaction details
• Full disclosure of recent insider sales for the past three months totaling 25,525 shares

Negative

• Proposed sale of 30,317 shares valued at $7,362,964.57 scheduled for 09/16/2025
• Insider has been selling repeatedly in recent months, which may be perceived negatively by some investors

Insights

Securities Analyst

TL;DR Insider intends to sell 30,317 GWRE shares valued at $7.36M; recent pattern shows regular dispositions over prior months.

The filing is a routine Rule 144 notice indicating an insider liquidation of restricted stock units received as compensation on 09/15/2025. The sale is routed through Morgan Stanley Smith Barney with an approximate execution date of 09/16/2025. The record of multiple prior sales totaling 25,525 shares in the past three months suggests an ongoing program of dispositions rather than a single one-off transaction. For investors, this is a disclosure of insider selling activity; no operational, financial performance, or forward guidance data is provided in the filing.

Corporate Governance Expert

TL;DR This is a compliance disclosure for insider sales of compensation-originated RSUs; it does not state any nonpublic adverse information.

The signer certifies there is no known material nonpublic information, and the filing documents that the securities were acquired as compensation and promptly filed for sale under Rule 144. The form names the broker and provides detailed transaction history for the prior three months, demonstrating transparency in insider trading reporting. The filing contains no mention of trading plans, 10b5-1 adoption dates, or other governance actions.

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

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	30317	7362964.57	84530578	09/16/2025	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	09/15/2025	Acquired as compensation - Restricted Stock Units	Issuer			30317	09/15/2025	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	09/15/2025	1400	353962
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	09/08/2025	1400	365792
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	09/02/2025	1400	300020
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	08/25/2025	1400	300580
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	08/18/2025	1400	296254
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	08/11/2025	1400	297416
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	08/04/2025	1400	315056
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/28/2025	1400	313250
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/21/2025	1400	311234
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/14/2025	1400	308910
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/07/2025	1400	322980
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/30/2025	1400	331646
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/23/2025	1400	333368
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/17/2025	5925	1474957.84
Michael George Rosenbaum c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/16/2025	1400	356342

144: Remarks and Signature

Remarks

Date of Notice

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does the Form 144 filed for GWRE report?

The form reports a proposed sale of 30,317 common shares of Guidewire (GWRE) through Morgan Stanley Smith Barney with an aggregate market value of $7,362,964.57 and an approximate sale date of 09/16/2025.

Who is the seller named in the Form 144 for GWRE?

The sales are reported for Michael George Rosenbaum c/o Guidewire Software, Inc., with multiple prior sales listed at the Guidewire address.

How were the securities acquired that are being sold?

The securities were acquired as compensation (Restricted Stock Units) on 09/15/2025 and are noted as paid/issued on the same date.

How many shares were sold by the insider in the past three months?

The filing discloses prior sales totaling 25,525 shares across multiple dates in June through September 2025, with gross proceeds listed for each transaction.

Which broker is handling the proposed sale?

The broker named is Morgan Stanley Smith Barney LLC Executive Financial Services located at 1 New York Plaza, 38th Floor, New York, NY, and the listed exchange is the NYSE.