[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Guidewire Software (GWRE) Form 144 discloses a proposed sale of 1,400 shares of Common stock with an aggregate market value of $297,416.00, to be offered approximately on 08/11/2025 on the NYSE through Morgan Stanley Smith Barney LLC. The filing shows 84,195,223 shares outstanding, providing scale for the disclosed sale.

The securities proposed for sale were acquired as restricted stock from the issuer on 12/15/2021. The filing identifies the selling party as Mike Rosenbaum (address listed) and lists multiple recent dispositions by the same person with dates and gross proceeds for each transaction reported in the filing.

Positive

• None.

Negative

• Insider dispositions disclosed: the filing lists multiple recent sales by Mike Rosenbaum with dates and gross proceeds, in addition to the proposed 1,400-share sale.

Insights

Securities Analyst

TL;DR: Routine insider sale notice; 1,400-share disposition proposed and multiple recent sales are disclosed.

The filing reports a small proposed sale of 1,400 shares valued at $297,416.00 and lists numerous prior dispositions by the same filer across recent months. Relative to the 84,195,223 shares outstanding shown, the single proposed block is a tiny fraction of outstanding equity, and the disclosure follows Rule 144 reporting conventions. The disclosure is factual and does not on its face show company operational changes or governance events.

Corporate Governance Expert

TL;DR: Multiple insider dispositions disclosed; filing notes restricted-stock origin and includes a 10b5-1 reference but no plan adoption date shown.

The securities to be sold were acquired as restricted stock from the issuer on 12/15/2021, and the filer certifies the representation about material nonpublic information. The form contains a 10b5-1 mention in the template, however no specific plan adoption date is populated in the filing content provided. The notice is procedural and documents the broker (Morgan Stanley Smith Barney LLC) and exchange (NYSE).

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	297416.00	84195223	08/11/2025	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	12/15/2021	Restricted Stock	ISSUER			1400	12/15/2021	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	08/04/2025	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	105	23342.55
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1	222.31
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1294	287669.14
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	339	80305.71
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/30/2025	1061	251340.29
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	45	11542.50
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	1355	347557.50
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	534	113218.68
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/27/2025	866	183609.32
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	1000	215250.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	400	86100.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/12/2025	1400	303114.00

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 propose to sell?

The Form 144 proposes the sale of 1,400 common shares with an aggregate market value of $297,416.00, approximately on 08/11/2025 on the NYSE.

Who is the filer listed on the Form 144 for GWRE?

The filing identifies Mike Rosenbaum as the person for whose account the securities are to be sold (address shown in the filing).

How and when were the securities to be sold originally acquired?

The securities were acquired as restricted stock from the issuer on 12/15/2021, with 1,400 shares noted in the acquisition table.

Which broker and exchange are named for the proposed sale?

The broker is Morgan Stanley Smith Barney LLC and the named exchange is the NYSE.

Does the filing show other recent sales by the same person?

Yes. The filing lists multiple dispositions by Mike Rosenbaum across recent dates, including a 5,925-share sale on 06/17/2025 with gross proceeds of $1,474,957.84 and many other transactions with amounts and gross proceeds shown.