[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Guidewire Software, Inc. (GWRE) shows proposed sale of 1,400 common shares through Morgan Stanley Smith Barney with an aggregate market value of $300,580, scheduled for 08/25/2025 on the NYSE. The filing identifies the securities as originally acquired on 03/15/2022 as restricted stock (999 shares) and performance shares (401 shares) from the issuer. The filer has executed multiple prior sales in the past three months, with individual transactions of 1,400 shares on several dates and a larger sale of 5,925 shares on 06/17/2025. The filing includes the standard representation that the seller is not aware of any undisclosed material adverse information about the issuer.

Positive

• Brokered sale through Morgan Stanley indicates orderly execution and compliance with Rule 144 procedures
• Acquisitions documented (restricted stock and performance shares dated 03/15/2022) support eligibility for resale

Negative

• Frequent insider sales over the past three months, including a 5,925-share sale on 06/17/2025, could be perceived negatively by some market participants

Insights

Securities Analyst

TL;DR: Routine insider disposition of equity; transaction sizes are small relative to shares outstanding but sales are frequent.

The filing documents a proposed sale of 1,400 shares valued at $300,580 to be executed through Morgan Stanley on 08/25/2025. Acquisition records show these shares originate from 2022 restricted and performance awards. The seller has made numerous similar-sized sales over recent weeks, plus a 5,925-share sale on 06/17/2025, indicating ongoing liquidity events rather than a single isolated disposition. Relative to the reported outstanding share count of 84,195,223, these individual sales are immaterial on a percentage basis, suggesting limited direct impact on capitalization. Investors should view this as insider liquidity rather than a signal of company fundamentals based solely on the filing.

Corporate Governance Specialist

TL;DR: Compliance appears in order; transactions routed through a broker and seller affirms no undisclosed material information.

The notice identifies Morgan Stanley Smith Barney as the broker and includes the required representations under Rule 144. Acquisition dates and types (restricted stock and performance shares dated 03/15/2022) are provided, supporting compliance with resale conditions. The repeated recent sales suggest either a systematic trading plan or scheduled dispositions; however, the filing itself does not state a 10b5-1 plan adoption date. From a governance perspective, filings are complete for required disclosures but do not provide context on any trading plan governance or firm-level implications.

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	300580.00	84195223	08/25/2025	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	Restricted Stock	ISSUER			999	03/15/2022	Not Applicable
Common	03/15/2022	Performance Shares	ISSUER			401	03/15/2022	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	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
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	1400	359100.00
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	1400	296828.00

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 the Form 144 filed for GWRE disclose?

The notice discloses a proposed sale of 1,400 common shares valued at $300,580 to be sold on 08/25/2025 through Morgan Stanley on the NYSE.

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

The filing lists Mike Rosenbaum at 970 Park Place, San Mateo CA, as the seller of the disclosed shares.

When were the shares being sold originally acquired?

The shares were acquired on 03/15/2022 as restricted stock (999 shares) and performance shares (401 shares) from the issuer.

Has the filer sold other GWRE shares recently?

Yes. The filing lists multiple sales in the past three months, typically 1,400 shares on several dates and a 5,925-share sale on 06/17/2025.

Does the Form 144 state a 10b5-1 trading plan adoption date?

No. The filing does not provide a plan adoption or instruction date for a 10b5-1 trading plan.