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      <liveTestFlag>LIVE</liveTestFlag>


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      <issuerCik>0001371285</issuerCik>
      <issuerName>TRUPANION, INC.</issuerName>
      <secFileNumber>001-36537</secFileNumber>
      <issuerAddress>
        <com:street1>6100 4TH AVENUE SOUTH</com:street1>
        <com:street2>SUITE 400</com:street2>
        <com:city>SEATTLE</com:city>
        <com:stateOrCountry>WA</com:stateOrCountry>
        <com:zipCode>98108</com:zipCode>
      </issuerAddress>
      <issuerContactPhone>855-727-9079</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>RAWLINGS DARRYL</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Officer</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common stock</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>Fidelity Brokerage Services LLC</name>
        <address>
          <com:street1>245 Summer Street</com:street1>
          <com:city>Boston</com:city>
          <com:stateOrCountry>MA</com:stateOrCountry>
          <com:zipCode>02110</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>4000</noOfUnitsSold>
      <aggregateMarketValue>141920.00</aggregateMarketValue>
      <noOfUnitsOutstanding>41020005</noOfUnitsOutstanding>
      <approxSaleDate>04/19/2023</approxSaleDate>
      <securitiesExchangeName>NASDAQ</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common stock</securitiesClassTitle>
      <acquiredDate>04/20/2007</acquiredDate>
      <natureOfAcquisitionTransaction>Founder shares acquired via gift</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Darryl Rawlings</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>Y</isGiftTransaction>
      <donarAcquiredDate>04/20/2007</donarAcquiredDate>
      <amountOfSecuritiesAcquired>4000</amountOfSecuritiesAcquired>
      <paymentDate>04/20/2007</paymentDate>
      <natureOfPayment>N/A</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Kuyashii Primary Equities LLC</name>
        <address>
          <com:street1>c/o Trupanion, Inc.</com:street1>
          <com:street2>6100 4th Avenue S, Suite 200</com:street2>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Trupanion, Inc.</securitiesClassTitle>
      <saleDate>01/26/2023</saleDate>
      <amountOfSecuritiesSold>4000</amountOfSecuritiesSold>
      <grossProceeds>217310.95</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Kuyashii Primary Equities LLC</name>
        <address>
          <com:street1>c/o Trupanion, Inc.</com:street1>
          <com:street2>6100 4th Avenue S, Suite 200</com:street2>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Trupanion, Inc.</securitiesClassTitle>
      <saleDate>02/13/2023</saleDate>
      <amountOfSecuritiesSold>4000</amountOfSecuritiesSold>
      <grossProceeds>234014.17</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Kuyashii Primary Equities LLC</name>
        <address>
          <com:street1>c/o Trupanion, Inc.</com:street1>
          <com:street2>6100 4th Avenue S, Suite 200</com:street2>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Trupanion, Inc.</securitiesClassTitle>
      <saleDate>02/28/2023</saleDate>
      <amountOfSecuritiesSold>4000</amountOfSecuritiesSold>
      <grossProceeds>232413.44</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Kuyashii Primary Equities LLC</name>
        <address>
          <com:street1>c/o Trupanion, Inc.</com:street1>
          <com:street2>6100 4th Avenue S, Suite 200</com:street2>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Trupanion, Inc.</securitiesClassTitle>
      <saleDate>03/16/2023</saleDate>
      <amountOfSecuritiesSold>4000</amountOfSecuritiesSold>
      <grossProceeds>220680.00</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Kuyashii Primary Equities LLC</name>
        <address>
          <com:street1>c/o Trupanion, Inc.</com:street1>
          <com:street2>6100 4th Avenue S, Suite 200</com:street2>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Trupanion, Inc.</securitiesClassTitle>
      <saleDate>04/04/2023</saleDate>
      <amountOfSecuritiesSold>4000</amountOfSecuritiesSold>
      <grossProceeds>164809.85</grossProceeds>
    </securitiesSoldInPast3Months>
    <remarks>shares sold for Kuyashii Primary Equities LLC, Darryl Rawlings as Manager</remarks>
    <noticeSignature>
      <noticeDate>04/19/2023</noticeDate>
      <planAdoptionDates>
        <planAdoptionDate>11/18/2022</planAdoptionDate>
      </planAdoptionDates>
      <signature>/s/ Myra King, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Darryl Rawlings</signature>
    </noticeSignature>
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144
0001611679
XXXXXXXX
LIVE
0001371285
TRUPANION, INC.
001-36537
6100 4TH AVENUE SOUTH
SUITE 400
SEATTLE
WA
98108
855-727-9079
RAWLINGS DARRYL
Officer
Common stock
Fidelity Brokerage Services LLC
245 Summer Street
Boston
MA
02110
4000
141920.00
41020005
04/19/2023
NASDAQ
Common stock
04/20/2007
Founder shares acquired via gift
Darryl Rawlings
Y
04/20/2007
4000
04/20/2007
N/A
N
Kuyashii Primary Equities LLC
c/o Trupanion, Inc.
6100 4th Avenue S, Suite 200
Seattle
WA
98108
Trupanion, Inc.
01/26/2023
4000
217310.95
Kuyashii Primary Equities LLC
c/o Trupanion, Inc.
6100 4th Avenue S, Suite 200
Seattle
WA
98108
Trupanion, Inc.
02/13/2023
4000
234014.17
Kuyashii Primary Equities LLC
c/o Trupanion, Inc.
6100 4th Avenue S, Suite 200
Seattle
WA
98108
Trupanion, Inc.
02/28/2023
4000
232413.44
Kuyashii Primary Equities LLC
c/o Trupanion, Inc.
6100 4th Avenue S, Suite 200
Seattle
WA
98108
Trupanion, Inc.
03/16/2023
4000
220680.00
Kuyashii Primary Equities LLC
c/o Trupanion, Inc.
6100 4th Avenue S, Suite 200
Seattle
WA
98108
Trupanion, Inc.
04/04/2023
4000
164809.85
shares sold for Kuyashii Primary Equities LLC, Darryl Rawlings as Manager
04/19/2023
11/18/2022
/s/ Myra King, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Darryl Rawlings