<?xml version="1.0" encoding="UTF-8"?><edgarSubmission xmlns="http://www.sec.gov/edgar/ownership" xmlns:com="http://www.sec.gov/edgar/common">
  <!-- Generated by Workiva -->
  <headerData>
    <submissionType>144</submissionType>
    <filerInfo>
      <filer>
        <filerCredentials>
          <cik>0001784996</cik>
          <ccc>XXXXXXXX</ccc>
        </filerCredentials>
      </filer>
      <liveTestFlag>LIVE</liveTestFlag>



    </filerInfo>
  </headerData>
  <formData>
    <issuerInfo>
      <issuerCik>0001528396</issuerCik>
      <issuerName>Guidewire Software, Inc.</issuerName>
      <secFileNumber>001-35394</secFileNumber>
      <issuerAddress>
        <com:street1>970 Park Pl</com:street1>
        <com:street2>Suite 200</com:street2>
        <com:city>San Mateo</com:city>
        <com:stateOrCountry>CA</com:stateOrCountry>
        <com:zipCode>94403</com:zipCode>
      </issuerAddress>
      <issuerContactPhone>650-357-9100</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>Michael George Rosenbaum</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Chief Executive Officer</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>Morgan Stanley Smith Barney LLC Executive Financial Services</name>
        <address>
          <com:street1>1 New York Plaza</com:street1>
          <com:street2>38th Floor</com:street2>
          <com:city>New York</com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10004</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>5925</noOfUnitsSold>
      <aggregateMarketValue>1474957.85</aggregateMarketValue>
      <noOfUnitsOutstanding>84195223</noOfUnitsOutstanding>
      <approxSaleDate>06/17/2025</approxSaleDate>
      <securitiesExchangeName>NYSE</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>06/15/2025</acquiredDate>
      <natureOfAcquisitionTransaction>Acquired as compensation - Restricted Stock Units</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Issuer</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>5925</amountOfSecuritiesAcquired>
      <paymentDate>06/17/2025</paymentDate>
      <natureOfPayment>N/A (acquired as compensation)</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/16/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>356342</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/09/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>359100</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/02/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>301490</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/27/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>296828</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/19/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>301350</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/12/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>303114</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/05/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>291704</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>04/28/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>277508</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>04/21/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>265216</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>04/14/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>272860</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>04/07/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>234948</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/31/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>258174</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/24/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>273210</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/18/2025</saleDate>
      <amountOfSecuritiesSold>4937</amountOfSecuritiesSold>
      <grossProceeds>935133.93</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Michael George Rosenbaum</name>
        <address>
          <com:street1>c/o Guidewire Software, Inc.</com:street1>
          <com:street2>970 Park Pl, Suite 200</com:street2>
          <com:city>San Mateo</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94403</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/17/2025</saleDate>
      <amountOfSecuritiesSold>1400</amountOfSecuritiesSold>
      <grossProceeds>259042</grossProceeds>
    </securitiesSoldInPast3Months>
    <noticeSignature>
      <noticeDate>06/17/2025</noticeDate>
      <signature>By: Winston King, Attorney-in-Fact for Michael George Rosenbaum</signature>
    </noticeSignature>
  </formData>
</edgarSubmission>
