[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) filed a Form 144 notifying of a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney (NYSE) with an aggregate market value of $342,370 and an approximate sale date of 09/22/2025. The filing shows those 1,400 shares were acquired as 735 performance shares on 06/15/2022 and 665 restricted shares on 03/15/2022, matching a total of 1,400 shares available for sale. The notice also lists prior open-market sales by Mike Rosenbaum totaling 48,517 shares across dates from 06/23/2025 to 09/16/2025 with gross proceeds shown for each transaction.

Positive

• Rule 144 compliance and transparency: The filing discloses the planned sale and prior transactions as required.
• Acquisition traceability: Acquisition dates and types (performance shares, restricted stock) are provided for the 1,400 shares to be sold.

Negative

• Substantial insider selling: The filer sold 48,517 shares in the past three months, which is a sizable volume of recent dispositions.
• Potential market pressure: Recent repeated sales by the same insider may increase sell-side supply, though the filing does not state remaining insider holdings.

Insights

Financial Analyst

TL;DR: Insider sales are material in size but the filing is a routine Rule 144 disclosure; it documents recent systematic dispositions totaling 48,517 shares.

The Form 144 provides explicit detail on a planned sale of 1,400 shares (market value $342,370) and lists prior sales by Mike Rosenbaum totaling 48,517 shares between 06/23/2025 and 09/16/2025. From a financial-analyst perspective, the filing is a transparency event rather than an operational update: it does not disclose company performance metrics, guidance, nor insider rationale. Investors should view this as an insider liquidity event documented to comply with securities rules; its market impact depends on the insider's remaining stake size relative to outstanding shares (outstanding shares are listed as 84,530,578).

Corporate Governance Expert

TL;DR: The filing complies with Rule 144 and includes acquisition dates for the securities, but frequent sales may raise governance questions about insider liquidity.

The notice correctly identifies the nature of the acquired securities (performance shares and restricted stock) and includes acquisition dates and amounts, satisfying disclosure requirements. The schedule of recent sales demonstrates recurring dispositions by the same insider across multiple weeks. While compliance is clear, repeated sales by an officer or affiliate can prompt investor questions about governance practices or personal liquidity needs; however, the form does not provide context or indicate any regulatory concerns.

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	342370.00	84530578	09/22/2025	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	Performance Shares	Issuer			735	06/15/2022	Not Applicable
Common	03/15/2022	Restricted Stock	Issuer			665	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	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
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

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 GWRE Form 144 filed by Mike Rosenbaum notify investors about?

The Form 144 notifies a proposed sale of 1,400 common shares with an aggregate market value of $342,370, approximate sale date 09/22/2025, and lists prior sales.

How many shares did Mike Rosenbaum sell in the past three months according to the filing?

The filing lists prior open-market sales totaling 48,517 shares between 06/23/2025 and 09/16/2025 with gross proceeds shown for each sale.

What types of shares are being sold in the proposed transaction on 09/22/2025?

The 1,400 shares to be sold were acquired as 735 performance shares (06/15/2022) and 665 restricted stock (03/15/2022).

Which broker is handling the proposed sale listed in the Form 144?

The broker named is Morgan Stanley Smith Barney LLC, Executive Financial Services, 1 New York Plaza and the exchange is listed as NYSE.

Does the Form 144 disclose outstanding shares for Guidewire (GWRE)?

Yes, the filing lists 84,530,578 shares outstanding in the securities information section.