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        <filerInfo>
            <filer>
                <filerCredentials>
                    <cik>0001478448</cik>
                    <ccc>XXXXXXXX</ccc>
                </filerCredentials>
            </filer>
            <liveTestFlag>LIVE</liveTestFlag>



        </filerInfo>
    </headerData>
    <formData>
        <issuerInfo>
            <issuerCik>0001446847</issuerCik>
            <issuerName>IRONWOOD PHARMACEUTICALS INC.</issuerName>
            <secFileNumber>001-34620</secFileNumber>
            <issuerAddress>
                <ns2:street1>100 SUMMER STREET, SUITE 2300</ns2:street1>
                <ns2:city>BOSTON</ns2:city>
                <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                <ns2:zipCode>02110</ns2:zipCode>
            </issuerAddress>
            <issuerContactPhone>(617) 621-7722</issuerContactPhone>
            <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>THOMAS MCCOURT</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
            <relationshipsToIssuer>
                <relationshipToIssuer>Officer</relationshipToIssuer>
                <relationshipToIssuer>Director</relationshipToIssuer>
            </relationshipsToIssuer>
        </issuerInfo>
        <securitiesInformation>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <brokerOrMarketmakerDetails>
                <name>E*TRADE FINANCIAL CORPORATION</name>
                <address>
                    <ns2:street1>3 EDISON DRIVE</ns2:street1>
                    <ns2:city>ALPHARETTA</ns2:city>
                    <ns2:stateOrCountry>GA</ns2:stateOrCountry>
                    <ns2:zipCode>30005</ns2:zipCode>
                </address>
            </brokerOrMarketmakerDetails>
            <noOfUnitsSold>26632</noOfUnitsSold>
            <aggregateMarketValue>284951.75</aggregateMarketValue>
            <noOfUnitsOutstanding>155346103</noOfUnitsOutstanding>
            <approxSaleDate>05/30/2023</approxSaleDate>
            <securitiesExchangeName>NASD</securitiesExchangeName>
        </securitiesInformation>
        <securitiesToBeSold>
            <securitiesClassTitle>COMMON</securitiesClassTitle>
            <acquiredDate>05/18/2023</acquiredDate>
            <natureOfAcquisitionTransaction>Restricted Stock</natureOfAcquisitionTransaction>
            <nameOfPersonfromWhomAcquired>ISSUER</nameOfPersonfromWhomAcquired>
            <isGiftTransaction>N</isGiftTransaction>
            <amountOfSecuritiesAcquired>26632</amountOfSecuritiesAcquired>
            <paymentDate>05/18/2023</paymentDate>
            <natureOfPayment>Not Applicable</natureOfPayment>
        </securitiesToBeSold>
        <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>THOMAS MCCOURT</name>
                <address>
                    <ns2:street1>100 SUMMER STREET, SUITE 2300</ns2:street1>
                    <ns2:city>BOSTON</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02110</ns2:zipCode>
                </address>
            </sellerDetails>
            <securitiesClassTitle>common</securitiesClassTitle>
            <saleDate>05/22/2023</saleDate>
            <amountOfSecuritiesSold>36000</amountOfSecuritiesSold>
            <grossProceeds>363558.00</grossProceeds>
        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>THOMAS MCCOURT</name>
                <address>
                    <ns2:street1>100 SUMMER STREET, SUITE 2300</ns2:street1>
                    <ns2:city>BOSTON</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02110</ns2:zipCode>
                </address>
            </sellerDetails>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>05/08/2023</saleDate>
            <amountOfSecuritiesSold>21148</amountOfSecuritiesSold>
            <grossProceeds>224653.09</grossProceeds>
        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>THOMAS MCCOURT</name>
                <address>
                    <ns2:street1>100 SUMMER STREET, SUITE 2300</ns2:street1>
                    <ns2:city>BOSTON</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02110</ns2:zipCode>
                </address>
            </sellerDetails>
            <securitiesClassTitle>common</securitiesClassTitle>
            <saleDate>03/27/2023</saleDate>
            <amountOfSecuritiesSold>46129</amountOfSecuritiesSold>
            <grossProceeds>489421.00</grossProceeds>
        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>THOMAS MCCOURT</name>
                <address>
                    <ns2:street1>100 SUMMER STREET, SUITE 2300</ns2:street1>
                    <ns2:city>BOSTON</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02110</ns2:zipCode>
                </address>
            </sellerDetails>
            <securitiesClassTitle>common</securitiesClassTitle>
            <saleDate>03/03/2023</saleDate>
            <amountOfSecuritiesSold>33756</amountOfSecuritiesSold>
            <grossProceeds>376805.00</grossProceeds>
        </securitiesSoldInPast3Months>
        <noticeSignature>
            <noticeDate>05/30/2023</noticeDate>
            <planAdoptionDates>
                <planAdoptionDate>12/12/2022</planAdoptionDate>
            </planAdoptionDates>
            <signature>/s/ Thomas McCourt</signature>
        </noticeSignature>
    </formData>
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144
0001478448
XXXXXXXX
LIVE
0001446847
IRONWOOD PHARMACEUTICALS INC.
001-34620
100 SUMMER STREET, SUITE 2300
BOSTON
MA
02110
(617) 621-7722
THOMAS MCCOURT
Officer
Director
Common
E*TRADE FINANCIAL CORPORATION
3 EDISON DRIVE
ALPHARETTA
GA
30005
26632
284951.75
155346103
05/30/2023
NASD
COMMON
05/18/2023
Restricted Stock
ISSUER
N
26632
05/18/2023
Not Applicable
N
THOMAS MCCOURT
100 SUMMER STREET, SUITE 2300
BOSTON
MA
02110
common
05/22/2023
36000
363558.00
THOMAS MCCOURT
100 SUMMER STREET, SUITE 2300
BOSTON
MA
02110
Common
05/08/2023
21148
224653.09
THOMAS MCCOURT
100 SUMMER STREET, SUITE 2300
BOSTON
MA
02110
common
03/27/2023
46129
489421.00
THOMAS MCCOURT
100 SUMMER STREET, SUITE 2300
BOSTON
MA
02110
common
03/03/2023
33756
376805.00
05/30/2023
12/12/2022
/s/ Thomas McCourt