[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Guidewire Software, Inc. (GWRE). The filer proposes to sell 1,400 common shares with an aggregate market value of $300,020.00 through Morgan Stanley Smith Barney on 09/02/2025 on the NYSE. The securities were acquired as restricted stock on 03/15/2022. The filing lists prior sales by the same person, totaling 22,725 shares sold between 06/09/2025 and 08/25/2025, with individual gross proceeds reported for each sale.

Positive

• Required disclosure provided: Filing lists sale date, broker, amounts, and proceeds, meeting Rule 144 notice requirements.
• Acquisition details included: Securities identified as restricted stock acquired 03/15/2022, which clarifies the nature of the holdings.

Negative

• Substantial insider sales: The filer sold a total of 22,725 shares from 06/09/2025 to 08/25/2025, which could be viewed as notable insider liquidity.
• Ongoing sales continue: A proposed sale of 1,400 shares on 09/02/2025 is reported, indicating further insider disposition.

Insights

Securities Analyst

TL;DR: Routine insider Form 144 discloses a proposed sale of 1,400 shares and substantial recent sales totaling 22,725 shares.

The filing is a standard Rule 144 notice showing the proposed disposition of restricted shares acquired on 03/15/2022. The planned sale of 1,400 shares valued at $300,020 is to occur through Morgan Stanley Smith Barney on 09/02/2025. The table of recent transactions shows multiple open-market sales between 06/09/2025 and 08/25/2025, aggregating 22,725 shares with gross proceeds reported per trade. From a compliance and disclosure perspective, the filing provides required sale dates, quantities, and proceeds, enabling market participants to verify insider liquidity events.

Corporate Governance Expert

TL;DR: The document documents repeated insider disposals and formal compliance with Rule 144 reporting requirements.

The filer represents no undisclosed material adverse information and identifies the nature of acquisition as restricted stock from the issuer on 03/15/2022. The repeated sales documented in the prior three months are clearly itemized with dates, amounts, and proceeds, which supports transparency. There is no additional contextual information in the filing (e.g., plan adoption date, motives, or trading plan) so governance interpretation should rely on these factual disclosures only.

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	300020.00	84195223	09/02/2025	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			1400	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	08/25/2025	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
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

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) disclose?

The Form 144 discloses a proposed sale of 1,400 common shares valued at $300,020.00, acquired as restricted stock on 03/15/2022, to be sold on 09/02/2025 via Morgan Stanley Smith Barney.

How many shares did the insider sell in the past three months?

The filing lists sales totaling 22,725 shares between 06/09/2025 and 08/25/2025, with individual gross proceeds reported for each trade.

Who is the broker handling the proposed sale?

The proposed sale is to be executed through Morgan Stanley Smith Barney LLC Executive Financial Services on the NYSE.

When were the securities originally acquired?

The securities to be sold were acquired as restricted stock on 03/15/2022 from the issuer.

Does the filing state any material nonpublic information?

By signing the notice, the person represents that they do not know any material adverse information about the issuer that has not been publicly disclosed; the filing contains no other material nonpublic disclosures.