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        <filerInfo>
            <filer>
                <filerCredentials>
                    <cik>0001624067</cik>
                    <ccc>XXXXXXXX</ccc>
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            <liveTestFlag>LIVE</liveTestFlag>



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        <issuerInfo>
            <issuerCik>0001505155</issuerCik>
            <issuerName>UPLAND SOFTWARE, INC.</issuerName>
            <secFileNumber>001-36720</secFileNumber>
            <issuerAddress>
                <ns2:street1>401 Congress Ave.,</ns2:street1>
                <ns2:street2>Suite 1850,</ns2:street2>
                <ns2:city>Austin,</ns2:city>
                <ns2:stateOrCountry>TX</ns2:stateOrCountry>
                <ns2:zipCode>78701</ns2:zipCode>
            </issuerAddress>
            <issuerContactPhone>(512) 960-1010</issuerContactPhone>
            <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>TIMOTHY WILLIAM MATTOX</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
            <relationshipsToIssuer>
                <relationshipToIssuer>Director</relationshipToIssuer>
            </relationshipsToIssuer>
        </issuerInfo>
        <securitiesInformation>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <brokerOrMarketmakerDetails>
                <name>Morgan Stanley Smith Barney LLC Executive Financial Services</name>
                <address>
                    <ns2:street1>1 New York Plaza</ns2:street1>
                    <ns2:street2>8th Floor</ns2:street2>
                    <ns2:city>New York</ns2:city>
                    <ns2:stateOrCountry>NY</ns2:stateOrCountry>
                    <ns2:zipCode>10004</ns2:zipCode>
                </address>
            </brokerOrMarketmakerDetails>
            <noOfUnitsSold>20000</noOfUnitsSold>
            <aggregateMarketValue>63862.00</aggregateMarketValue>
            <noOfUnitsOutstanding>28168267</noOfUnitsOutstanding>
            <approxSaleDate>03/17/2025</approxSaleDate>
            <securitiesExchangeName>NASDAQ</securitiesExchangeName>
        </securitiesInformation>
        <securitiesToBeSold>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <acquiredDate>12/16/2018</acquiredDate>
            <natureOfAcquisitionTransaction>Restricted Stock</natureOfAcquisitionTransaction>
            <nameOfPersonfromWhomAcquired>ISSUER</nameOfPersonfromWhomAcquired>
            <isGiftTransaction>N</isGiftTransaction>
            <amountOfSecuritiesAcquired>20000</amountOfSecuritiesAcquired>
            <paymentDate>12/16/2018</paymentDate>
            <natureOfPayment>Not Applicable</natureOfPayment>
        </securitiesToBeSold>
        <nothingToReportFlagOnSecuritiesSoldInPast3Months>Y</nothingToReportFlagOnSecuritiesSoldInPast3Months>
        <noticeSignature>
            <noticeDate>03/17/2025</noticeDate>
            <planAdoptionDates>
                <planAdoptionDate>11/22/2024</planAdoptionDate>
            </planAdoptionDates>
            <signature>/s/ Timothy William Mattox</signature>
        </noticeSignature>
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144
0001624067
XXXXXXXX
LIVE
0001505155
UPLAND SOFTWARE, INC.
001-36720
401 Congress Ave.,
Suite 1850,
Austin,
TX
78701
(512) 960-1010
TIMOTHY WILLIAM MATTOX
Director
Common
Morgan Stanley Smith Barney LLC Executive Financial Services
1 New York Plaza
8th Floor
New York
NY
10004
20000
63862.00
28168267
03/17/2025
NASDAQ
Common
12/16/2018
Restricted Stock
ISSUER
N
20000
12/16/2018
Not Applicable
Y
03/17/2025
11/22/2024
/s/ Timothy William Mattox