[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for GWRE (Guidewire Software, Inc.) reports proposed and recent insider sales. The notice shows a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney with an aggregate market value of $353,962, with an approximate sale date of 09/15/2025 on the NYSE. The filing lists total shares outstanding of 84,530,578. Acquisition details show 100 restricted shares acquired 09/15/2021 and 1,300 restricted shares acquired 03/15/2022.

The filing also discloses multiple prior sales by the same seller, Mike Rosenbaum, across June–September 2025, including a larger sale of 5,925 shares on 06/17/2025, and several 1,400-share transactions with reported gross proceeds for each sale.

Positive

• Disclosure completeness: The filing specifies broker, share amounts, aggregate market value, approximate sale date, and shares outstanding.
• Acquisition detail provided: Dates and nature of acquisition (restricted stock) for the securities to be sold are disclosed.

Negative

• Frequent insider sales: Multiple sales by Mike Rosenbaum in June–September 2025, including a 5,925-share sale, may signal notable insider liquidity.
• Potential market perception risk: Repeated sales in a short period could be perceived negatively by investors, despite compliance with Rule 144.

Insights

Financial Analyst

TL;DR: Repeated insider sales reported; single proposed sale is modest versus total shares outstanding.

The filing documents a proposed sale of 1,400 shares valued at $353,962 and confirms the issuer's outstanding share count at 84,530,578. For a financial analyst, the proposed sale size is immaterial relative to outstanding shares (approximately 0.0017%). However, the series of recent sales by the same individual, including a 5,925-share transaction, suggests ongoing insider liquidity activity that may warrant monitoring for pattern or timing relative to corporate disclosures.

Corporate Governance Expert

TL;DR: Multiple insider sales under Rule 144 are disclosed; frequency may raise governance questions but not necessarily a violation.

The notice properly identifies the broker, sale dates, acquisition dates, and the nature of the holdings (restricted stock). Frequent sales by an insider within a short period increase disclosure relevance for shareholders assessing insider behavior. The form includes the required certification that the seller is unaware of undisclosed material adverse information, which is standard.

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	353962.00	84530578	09/15/2025	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	09/15/2021	Restricted Stock	Issuer			100	09/15/2021	Not Applicable
Common	03/15/2022	Restricted Stock	Issuer			1300	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	09/08/2025	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
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

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 GWRE report?

The form reports a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney with aggregate market value of $353,962 and lists 84,530,578 shares outstanding.

Who is the seller named in the filing?

The seller is identified as Mike Rosenbaum with an address of 970 Park Place, Suite 200, San Mateo, CA.

When were the securities being offered acquired?

The securities to be sold were acquired as restricted stock: 100 shares on 09/15/2021 and 1,300 shares on 03/15/2022.

What recent sales by the insider are disclosed?

The filing lists multiple sales from 06/16/2025 to 09/08/2025, including a 5,925-share sale on 06/17/2025 and several 1,400-share transactions.

On which exchange will the proposed sale occur?

The proposed sale is scheduled for the NYSE with an approximate sale date of 09/15/2025.