[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Guidewire Software, Inc. (GWRE) reports a proposed sale of 7,535 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $1,874,377.21 and approximately 84,530,578 shares outstanding.

The securities were acquired on 09/15/2025 as 1,544 restricted stock and 5,991 performance shares, with payment noted as Not Applicable. The filing also discloses a sale on 09/16/2025 by Jeffrey Cooper of 14,103 shares for gross proceeds of $3,425,148.80. The filer represents they are not aware of any undisclosed material adverse information and includes the standard signature and criminal-statement notice.

Positive

• Required disclosures provided including acquisition dates, share counts, broker, and aggregate market value
• Attestation included that the seller does not possess undisclosed material adverse information

Negative

• Insider sale disclosed by Jeffrey Cooper of 14,103 shares for gross proceeds of $3,425,148.80 (may attract investor attention)

Insights

Financial Analyst

TL;DR: Small proposed sale relative to outstanding shares; recent insider sale disclosed.

The proposed sale of 7,535 shares represents roughly 0.009% of the reported 84,530,578 shares outstanding, indicating the transaction is immaterial to total equity supply. The filing shows the lots were acquired on 09/15/2025 and consist of restricted and performance awards, typical for executive compensation monetization. The separate disclosed sale of 14,103 shares on 09/16/2025 produced gross proceeds of $3,425,148.80, which is a larger absolute transaction but still small versus total shares outstanding. For investors, these are routine insider sales with no additional financial results or forward guidance disclosed.

Corporate Governance Expert

TL;DR: Filing follows Rule 144 mechanics; includes standard insider representation about non-public material information.

The Form 144 documents proposed Rule 144 sales and includes the required attestation that the seller is unaware of undisclosed material adverse information. The securities were issued by the issuer and acquired on 09/15/2025 as restricted and performance shares, suggesting internal compensation-related origin rather than open-market purchases. The presence of a recent sale by Jeffrey Cooper is disclosed, and dates and amounts are provided, fulfilling disclosure obligations under Rule 144.

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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	7535	1874377.21	84530578	09/18/2025	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	Restricted Stock	ISSUER			1544	09/15/2025	Not Applicable
Common	09/15/2025	Performance Shares	ISSUER			5991	09/15/2025	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
JEFFREY COOPER 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/16/2025	14103	3425148.80

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 does the Form 144 for Guidewire Software (GWRE) report?

The form reports a proposed sale of 7,535 common shares through Morgan Stanley Smith Barney LLC with an aggregate market value of $1,874,377.21.

When were the shares to be sold by the filer acquired?

The shares were acquired on 09/15/2025 as restricted stock (1,544) and performance shares (5,991).

What broker is handling the proposed sale?

The proposed sale is to be handled by Morgan Stanley Smith Barney LLC at 1 New York Plaza, 8th Floor, New York, NY 10004.

Has any related sale occurred recently?

Yes, the filing discloses that Jeffrey Cooper sold 14,103 common shares on 09/16/2025 for gross proceeds of $3,425,148.80.

How large is the proposed sale relative to shares outstanding?

The proposed sale of 7,535 shares is approximately 0.009% of the reported 84,530,578 shares outstanding.