[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) has filed a Form 144, indicating the intended sale of 1,585 common shares with an aggregate market value of $395,380.31. The planned trade is scheduled for 18 June 2025 through Morgan Stanley Smith Barney on the NYSE. The filing also discloses that the same insider—identified in prior sales data as Jeffrey Cooper—has sold 4,933 shares for total proceeds of $1.11 million over the last three months (2,826 shares on 17 June 2025 and 2,107 shares on 19 March 2025).

The proposed sale represents less than 0.002 % of GWRE’s outstanding 84.2 million shares, suggesting limited dilution or market-supply impact. No relationship to the issuer or additional adverse information was provided, and the filer affirmed that no undisclosed material information is known. While insider sales can sometimes be viewed negatively, the relatively small size versus float keeps the market impact minimal.

Positive

• None.

Negative

• Continued insider selling: Filing follows 4,933 shares already sold in the past three months, potentially signaling reduced insider confidence, though dollar value is modest.

Insights

Securities Analyst

TL;DR: Minor insider sale (1,585 shares) after recent disposals; size immaterial, sentiment mildly negative, overall market impact negligible.

The Form 144 signals another planned disposition by insider Jeffrey Cooper, adding to 4,933 shares already sold in the past quarter. The cumulative 6,518-share program is worth roughly $1.5 million, modest against GWRE’s $9-plus billion market cap and 84 million shares outstanding. No price, earnings, or operational data accompany the notice, so valuation fundamentals remain unchanged. Still, serial insider selling can be interpreted as lukewarm confidence, warranting monitoring by investors, although the transaction’s scale is far too small to affect liquidity or valuation metrics.

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

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	1585	395380.31	84195223	06/18/2025	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	06/15/2025	Restricted Stock	ISSUER			1585	06/15/2025	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
JEFFREY COOPER 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/17/2025	2826	703498.81
JEFFREY COOPER 970 Park Place, Suite 200 San Mateo CA 94403	Common	03/19/2025	2107	407061.87

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

How many Guidewire (GWRE) shares are being sold under this Form 144?

1,585 common shares are slated for sale.

What is the approximate value of the GWRE shares to be sold?

The aggregate market value is $395,380.31.

When is the planned sale date for these GWRE shares?

The filer listed June 18, 2025 as the approximate sale date.

Which broker will execute the GWRE insider sale?

Morgan Stanley Smith Barney LLC will handle the transaction.

How many GWRE shares has the insider sold in the last three months?

A total of 4,933 shares were sold prior to this notice.