[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Form 144 filing by an insider of Guidewire Software, Inc. (GWRE) reports a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney with an aggregate market value of $296,254, to be sold on or about 08/18/2025 on the NYSE. The filer discloses acquisition details showing these shares were originally granted by the issuer as performance shares (1,294) on 03/15/2022 and restricted stock (106) on 12/15/2021. The filing also lists numerous recent open-market sales by the same person between 05/19/2025 and 08/11/2025, including a large sale of 5,925 shares on 06/17/2025 for $1,474,957.84. The notice includes the insider representation required under Rule 144 that no undisclosed material adverse information is known.

Positive

• Full Rule 144 compliance: Broker, share counts, sale date, and grant history are disclosed.
• Transparency on acquisition source: Specifies shares were issued by the issuer as performance shares and restricted stock.
• Detailed prior-sale history: Lists multiple recent open-market sales with dates and gross proceeds, aiding investor transparency.

Negative

• Significant recent insider selling: Multiple sales including a large 5,925-share transaction for $1,474,957.84 could be viewed negatively by some investors.
• Insufficient context on remaining insider holdings: The filing does not state the filer’s total post-sale ownership, limiting assessment of materiality.

Insights

Securities Analyst

TL;DR: Routine Rule 144 insider sale disclosure; several recent open-market disposals indicate ongoing monetization of equity holdings.

The filing is a standard Rule 144 notice describing a proposed sale of 1,400 common shares with an aggregate value of $296,254 scheduled for 08/18/2025 and confirms the shares were issued by the company as performance and restricted awards in 2021–2022. The detailed list of prior sales between 05/19/2025 and 08/11/2025, including a notable 5,925-share sale on 06/17/2025 for $1,474,957.84, shows the insider has been executing multiple transactions over recent months. For investors, this is transparent compliance with SEC resale rules rather than a corporate action; materiality depends on context relative to total insider holdings, which is not provided here.

Corporate Governance Expert

TL;DR: Proper disclosure of insider sales and grant origins; raises governance questions about timing but provides required attestations.

The notice appropriately identifies the broker, planned sale date, share class, share counts, and grant history (performance shares and restricted stock), and includes the certification that no undisclosed material adverse information exists. While the filing itself is procedurally compliant, the sequence of multiple recent sales may prompt stakeholders to review insider holding schedules and company disclosure cadence to assess alignment with governance and retention objectives. The filing does not provide any nonpublic operational details.

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	296254.00	84195223	08/18/2025	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	03/15/2022	Performance Shares	ISSUER			1294	03/15/2022	Not Applicable
Common	12/15/2021	Restricted Stock	ISSUER			106	12/15/2021	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	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	105	23342.55
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1	222.31
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1294	287669.14
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	339	80305.71
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/30/2025	1061	251340.29
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/23/2025	1400	333368.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/17/2025	5925	1474957.84
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/16/2025	1400	356342.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	45	11542.50
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	1355	347557.50
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/02/2025	1400	301490.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/27/2025	534	113218.68
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/27/2025	866	183609.32
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	1000	215250.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	400	86100.00

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 does Guidewire (GWRE) Form 144 filed on this notice disclose?

The filing discloses a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney with an aggregate market value of $296,254, planned for 08/18/2025.

Where did the shares being sold by the insider originate?

The filing states the shares were granted by the issuer: 1,294 performance shares (03/15/2022) and 106 restricted shares (12/15/2021).

Has the insider sold other GWRE shares recently?

Yes. The filing lists multiple recent sales from 05/19/2025 to 08/11/2025, including a 5,925-share sale on 06/17/2025 for $1,474,957.84.

Which broker will handle the proposed sale?

The broker named in the filing is Morgan Stanley Smith Barney LLC, Executive Financial Services, 1 New York Plaza, 8th Floor, New York, NY 10004.

Does the filer attest to knowledge of undisclosed material information?

Yes. The filer signs the representation that they do not know any material adverse information about the issuer that has not been publicly disclosed.