[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Guidewire Software insider sale notice: an individual proposes to sell 1,400 common shares on 10/06/2025 through Morgan Stanley Smith Barney LLC. The filing shows those 1,400 shares have an aggregate market value of $322,112.00 and the issuer has 84,530,578 shares outstanding. The securities were acquired as restricted stock on 06/15/2022.

The filing also lists multiple recent open-market sales by the same holder between 07/07/2025 and 09/29/2025, including a larger block of 30,317 shares sold on 09/16/2025 for $7,362,962.35. The notice includes the signer’s representation that they are not aware of undisclosed material adverse information.

Positive

• Transaction disclosed under Rule 144, providing transparency on planned resale
• Securities were acquired as restricted stock on 06/15/2022, indicating a standard vesting/source

Negative

• Substantial prior sale of 30,317 shares on 09/16/2025 for $7,362,962.35, showing recent insider liquidity
• Multiple recent sales from 07/07/2025 to 09/29/2025, which may increase free float

Insights

Equity Trading Specialist

TL;DR: Small planned sale and notable recent insider selling, likely routine liquidity rather than corporate change.

The filing records a proposed sale of 1,400 shares via Morgan Stanley Smith Barney LLC on 10/06/2025 with an aggregate market value of $322,112.00. The shares were acquired as restricted stock on 06/15/2022, which explains use of a Rule 144 notice to satisfy resale conditions.

Recent open-market disposals by the same holder include multiple 1,400-share lots and one block of 30,317 shares on 09/16/2025 for $7,362,962.35. Continued sales can increase free float in the near term; monitor trading volume and share-price reaction over the next 2-4 weeks.

Corporate Governance Analyst

TL;DR: Disclosure meets Rule 144 formalities; signer certifies no undisclosed material information.

The form documents the nature of acquisition (restricted stock on 06/15/2022) and provides a standard representation that the seller is unaware of material nonpublic information. This is the typical corporate-governance declaration required for compliant resale under Rule 144.

If insider selling persists at similar scale to the 30,317-share block on 09/16/2025, investors may view aggregate insider liquidity as noteworthy; monitor subsequent Form 144 or Form 4 filings over the next 1-3 months for pattern confirmation.

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	322112.00	84530578	10/06/2025	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			1400	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	09/29/2025	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
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

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 Guidewire (GWRE) disclose?

The notice reports a proposed sale of 1,400 common shares on 10/06/2025 via Morgan Stanley Smith Barney LLC with aggregate value $322,112.00.

When were the shares being sold by the GWRE insider acquired?

The securities were acquired as restricted stock on 06/15/2022, per the filing.

Has this insider sold other GWRE shares recently?

Yes; the filing lists multiple sales between 07/07/2025 and 09/29/2025, including 30,317 shares sold on 09/16/2025 for $7,362,962.35.

How many GWRE shares are outstanding according to the form?

The filing reports 84,530,578 shares outstanding.

Does the filer state they know of any undisclosed material information?

The signer represents that they do not know any material adverse information about the issuer that has not been publicly disclosed.