[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Guidewire Software (GWRE): Form 144 insider sale notice. An affiliate, Mike Rosenbaum, filed to sell 1,400 common shares with an aggregate market value of $305,942, through Morgan Stanley Smith Barney LLC. The filing lists an approximate sale date of 11/10/2025 on the NYSE.

The notice also details recent activity under Rule 144. Over the past three months, Rosenbaum reported multiple sales, including 30,317 shares on 09/16/2025 for $7,362,962.35, alongside several 1,400‑share transactions with disclosed gross proceeds for each date. The securities slated for the new sale were acquired as performance shares on 09/15/2022.

Insights

Securities law analyst

Routine Form 144: affiliate plans to sell 1,400 GWRE shares.

Form 144 is a notice by an affiliate intending to sell restricted or control securities under Rule 144. This filing lists 1,400 common shares to be sold via Morgan Stanley Smith Barney LLC, with an approximate sale date of 11/10/2025 on the NYSE and an aggregate market value of $305,942.

The excerpt also itemizes prior sales in the last three months, including a larger 30,317‑share transaction on 09/16/2025 for $7,362,962.35, plus several 1,400‑share sales on specified dates with stated gross proceeds. Actual market impact depends on execution details and holder decisions.

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	305942.00	84530578	11/10/2025	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	09/15/2022	Performance Shares	Issuer			1400	09/15/2022	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	11/03/2025	1400	324590.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/27/2025	1400	357560.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/20/2025	1400	343980.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/13/2025	1400	335594.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/06/2025	1400	322112.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/29/2025	1400	325150.00
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

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 did GWRE disclose in this Form 144?

An affiliate, Mike Rosenbaum, filed to sell 1,400 common shares with an aggregate market value of $305,942 on the NYSE.

When is the proposed sale date for GWRE shares in the Form 144?

The filing lists an approximate sale date of 11/10/2025.

Which broker is handling the proposed GWRE share sale?

The broker is Morgan Stanley Smith Barney LLC (Executive Financial Services).

What prior insider sales are disclosed for GWRE in the past 3 months?

Entries include 30,317 shares on 09/16/2025 for $7,362,962.35, plus multiple 1,400‑share sales with listed gross proceeds.

How were the GWRE shares being sold acquired?

They were acquired as performance shares on 09/15/2022.

On which exchange are the GWRE shares listed for this sale?

The filing names the NYSE as the securities exchange.