[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Insider sale notice for Guidewire Software, Inc. (GWRE): The filing reports proposed and recent sales of common stock by Mike Rosenbaum through Morgan Stanley Smith Barney. The current notice lists a proposed sale of 1,400 shares with an aggregate market value of $325,150 to be executed on 09/29/2025 on the NYSE. The filer also discloses multiple actual sales within the prior three months, including a large sale of 30,317 shares on 09/16/2025 generating gross proceeds of $7,362,962.35. The securities being sold were originally acquired on 06/15/2022 as restricted stock (777 shares) and performance shares (623 shares).

Positive

• None.

Negative

• Large insider disposition: A sale of 30,317 shares on 09/16/2025 produced gross proceeds of $7,362,962.35.
• Frequent recent sales: Multiple sales across June–September 2025 totaling tens of thousands of shares, which may increase share supply in short periods.

Insights

Securities Analyst

TL;DR: The filing documents routine insider dispositions, including a sizable sale on 09/16/2025, with no new company events disclosed.

The notice is a Rule 144 disclosure of proposed and completed sales by an insider representative. The largest reported transaction in the three-month history is material in absolute dollar terms (over $7.3 million), but the filing does not state any company operational or financial developments. These appear to be sales of previously granted restricted and performance shares acquired on 06/15/2022. From a market-impact perspective, such insider liquidity can be notable for short windows, though the form itself provides no indication of changed fundamentals.

Corporate Governance Expert

TL;DR: Multiple Rule 144 sales are disclosed; disclosures comply with standard insider-sale reporting requirements.

The form lists broker information, acquisition dates, nature of acquisition, and aggregated recent sales as required. The filer attests there is no undisclosed material adverse information. The filing documents sales executed through an institutional broker on the NYSE and shows the securities originated from issuer grants, indicating routine compensation-related disposition rather than third-party transfers or gifts. No governance actions or plan-adoption details (e.g., 10b5-1 plan date) are provided in the filing.

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

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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	1400	325150.00	84530578	09/29/2025	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	06/15/2022	Restricted Stock	ISSUER			777	06/15/2022	Not Applicable
Common	06/15/2022	Performance Shares	ISSUER			623	06/15/2022	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	09/22/2025	1400	342370.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/16/2025	30317	7362962.35
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/15/2025	1400	353962.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/08/2025	1400	365792.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/02/2025	1400	300020.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/25/2025	1400	300580.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/18/2025	1400	296254.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/11/2025	1400	297416.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/04/2025	1400	315056.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/28/2025	1400	313250.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1400	311234.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/14/2025	1400	308910.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/07/2025	1400	322980.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/30/2025	1400	331646.00

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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 insider is selling shares of Guidewire Software (GWRE)?

The filer is Mike Rosenbaum, who is selling shares through Morgan Stanley Smith Barney.

How many shares are proposed for sale in this Form 144 notice?

The proposed sale listed in this notice is 1,400 shares with an aggregate market value of $325,150, planned for 09/29/2025 on the NYSE.

What recent insider sales does the filing disclose for GWRE?

The filing discloses multiple sales from 06/30/2025 to 09/22/2025, including a significant sale of 30,317 shares on 09/16/2025 for $7,362,962.35.

When were the sold shares originally acquired?

The securities being sold were acquired on 06/15/2022 as restricted stock (777 shares) and performance shares (623 shares).

Does the filing indicate the insider adopted a 10b5-1 trading plan?

No 10b5-1 plan adoption date or instruction date is provided in the filing.