Insider plans $286,930 sale of common stock under Rule 144

Mike Rosenbaum filed a notice of proposed sale under Rule 144 to sell 1,400 shares of common stock through Morgan Stanley Smith Barney on the NYSE, with an aggregate market value of $286,930.00.

Rhea-AI Filing Summary

Mike Rosenbaum filed a notice of proposed sale under Rule 144 to sell 1,400 shares of common stock through Morgan Stanley Smith Barney on the NYSE, with an aggregate market value of $286,930.00. The filing states that these shares were acquired as performance shares from the issuer on 09/15/2022, with payment also dated that day and described as not applicable for cash terms.

Over the past three months, the notice lists a series of prior sales of the issuer’s common stock by Mike Rosenbaum, including 6,015 shares sold on 12/16/2025 for gross proceeds of $1,155,337.74, along with multiple 1,400‑share transactions on various dates. The issuer reports 85,019,176 shares of this class outstanding.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the Form 144 filing for GWRE disclose about planned stock sales?

The filing shows that Mike Rosenbaum plans to sell 1,400 shares of the issuer’s common stock through Morgan Stanley Smith Barney on the NYSE, with an aggregate market value of $286,930.00.

How were the GWRE shares in this Form 144 acquired?

The 1,400 shares covered by the notice were acquired on 09/15/2022 as performance shares from the issuer, with the nature of payment marked as not applicable.

What GWRE insider sales have occurred in the last three months according to this notice?

The notice lists multiple prior sales of the issuer’s common stock by Mike Rosenbaum over the last three months, including 6,015 shares sold on 12/16/2025 for gross proceeds of $1,155,337.74, plus several separate 1,400‑share transactions on earlier dates.

How many GWRE shares are outstanding according to the Form 144 content?

The securities information section reports 85,019,176 shares of the issuer’s common stock outstanding.

Which broker and exchange are used for the GWRE Form 144 planned sale?

The planned sale will be executed through Morgan Stanley Smith Barney LLC Executive Financial Services, with the common stock listed on the NYSE.

Who is the selling security holder in this GWRE Form 144 filing?

The selling security holder identified in the notice is Mike Rosenbaum, with an address at 970 Park Place, Suite 200, San Mateo, CA 94403.

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Accepted by SEC EDGAR 12/29/2025 - 04:01 PM Learn about SEC filing dates

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	0001784996
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	GUIDEWIRE SOFTWARE, INC.
SEC File Number	001-35394
Address of Issuer	970 Park Place, Suite 200 San Mateo CALIFORNIA 94403
Phone	(650) 357-9100
Name of Person for Whose Account the Securities are To Be Sold	MIKE ROSENBAUM
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	Officer
Relationship to Issuer	Director

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	286930.00	85019176	12/29/2025	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	09/15/2022	Performance Shares	ISSUER			1400	09/15/2022	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	12/22/2025	1400	281008.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	12/16/2025	6015	1155337.74
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	12/15/2025	1400	286076.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	12/08/2025	1400	295218.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	12/01/2025	1400	298816.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	11/24/2025	1400	298522.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	11/17/2025	1400	311556.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	11/10/2025	1400	305942.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	11/03/2025	1400	324590.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/27/2025	1400	357560.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/20/2025	1400	343980.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/13/2025	1400	335594.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/06/2025	1400	322112.00

144: Remarks and Signature

Remarks
Date of Notice	12/29/2025
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	10/15/2024
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	/s/ Michael George Rosenbaum
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)