<SEC-DOCUMENT>0001959173-25-005818.txt : 20250908
<SEC-HEADER>0001959173-25-005818.hdr.sgml : 20250908
<ACCEPTANCE-DATETIME>20250908095005
ACCESSION NUMBER:		0001959173-25-005818
CONFORMED SUBMISSION TYPE:	144/A
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20250908
DATE AS OF CHANGE:		20250908

SUBJECT COMPANY:	

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			TRUPANION, INC.
		CENTRAL INDEX KEY:			0001371285
		STANDARD INDUSTRIAL CLASSIFICATION:	HOSPITAL & MEDICAL SERVICE PLANS [6324]
		ORGANIZATION NAME:           	02 Finance
		EIN:				000000000
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		144/A
		SEC ACT:		1933 Act
		SEC FILE NUMBER:	001-36537
		FILM NUMBER:		251298816

	BUSINESS ADDRESS:	
		STREET 1:		6100 4TH AVENUE SOUTH
		STREET 2:		SUITE 400
		CITY:			SEATTLE
		STATE:			WA
		ZIP:			98108
		BUSINESS PHONE:		888-733-2685

	MAIL ADDRESS:	
		STREET 1:		6100 4TH AVENUE SOUTH
		STREET 2:		SUITE 400
		CITY:			SEATTLE
		STATE:			WA
		ZIP:			98108

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	TRUPANION INC.
		DATE OF NAME CHANGE:	20131114

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	VETINSURANCE INTERNATIONAL INC
		DATE OF NAME CHANGE:	20060802

REPORTING-OWNER:	

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			RAWLINGS DARRYL
		CENTRAL INDEX KEY:			0001611679
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		144/A

	MAIL ADDRESS:	
		STREET 1:		6100 4TH AVENUE SOUTH
		STREET 2:		SUITE 200
		CITY:			SEATTLE
		STATE:			WA
		ZIP:			98108
</SEC-HEADER>
<DOCUMENT>
<TYPE>144/A
<SEQUENCE>1
<FILENAME>primary_doc.xml
<TEXT>
<XML>
<?xml version="1.0" encoding="UTF-8"?><edgarSubmission xmlns="http://www.sec.gov/edgar/ownership" xmlns:com="http://www.sec.gov/edgar/common">
  <headerData>
    <submissionType>144/A</submissionType>
    <previousAccessionNumber>0001959173-25-005778</previousAccessionNumber>
    <filerInfo>
      <filer>
        <filerCredentials>
          <cik>0001611679</cik>
          <ccc>XXXXXXXX</ccc>
        </filerCredentials>
      </filer>
      <liveTestFlag>LIVE</liveTestFlag>



    </filerInfo>
  </headerData>
  <formData>
    <issuerInfo>
      <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>888-733-2685</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>RAWLINGS DARRYL</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Director</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common</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>30369</noOfUnitsSold>
      <aggregateMarketValue>1357943.00</aggregateMarketValue>
      <noOfUnitsOutstanding>4299467</noOfUnitsOutstanding>
      <approxSaleDate>09/04/2025</approxSaleDate>
      <securitiesExchangeName>NASDAQ</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award </natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion </nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2925</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2021</paymentDate>
      <natureOfPayment>Compensation </natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/22/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>54</amountOfSecuritiesAcquired>
      <paymentDate>02/22/2021</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2020</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2062</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2020</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>6743</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2021</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2926</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2021</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2022</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>11037</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2022</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>05/25/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2925</amountOfSecuritiesAcquired>
      <paymentDate>05/25/2021</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2022</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>3847</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2022</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>05/25/2022</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>3846</amountOfSecuritiesAcquired>
      <paymentDate>05/25/2022</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2020</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2062</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2020</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2023</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>7560</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2023</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2024</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>6308</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2024</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2022</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>3846</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2022</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2021</acquiredDate>
      <natureOfAcquisitionTransaction>Stock option</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>439</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2021</paymentDate>
      <natureOfPayment>cash/check</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2024</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>7517</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2024</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2019</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>740</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2019</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2020</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2062</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2020</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2020</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>5382</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2020</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2025</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>3684</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2025</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>05/25/2019</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>740</amountOfSecuritiesAcquired>
      <paymentDate>05/25/2019</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2023</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>4376</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2023</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/25/2019</acquiredDate>
      <natureOfAcquisitionTransaction>Stock</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>2959</amountOfSecuritiesAcquired>
      <paymentDate>02/25/2019</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>02/22/2025</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>7500</amountOfSecuritiesAcquired>
      <paymentDate>02/22/2025</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/25/2023</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>4259</amountOfSecuritiesAcquired>
      <paymentDate>11/25/2023</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/19/2018</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion	</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>100477</amountOfSecuritiesAcquired>
      <paymentDate>11/19/2018</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>11/12/2018</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>100477</amountOfSecuritiesAcquired>
      <paymentDate>11/12/2018</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>08/25/2019</acquiredDate>
      <natureOfAcquisitionTransaction>Stock award	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Trupanion</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>740</amountOfSecuritiesAcquired>
      <paymentDate>08/25/2019</paymentDate>
      <natureOfPayment>Compensation</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Darryl Rawlings c/o Trupanion </name>
        <address>
          <com:street1>6100 4th avenue South STE 400</com:street1>
          <com:city>Seattle</com:city>
          <com:stateOrCountry>WA</com:stateOrCountry>
          <com:zipCode>98108</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock </securitiesClassTitle>
      <saleDate>09/03/2025</saleDate>
      <amountOfSecuritiesSold>19631</amountOfSecuritiesSold>
      <grossProceeds>878487.25</grossProceeds>
    </securitiesSoldInPast3Months>
    <remarks>shares are being sold form Kuyashii Primary Equities LLC</remarks>
    <noticeSignature>
      <noticeDate>09/08/2025</noticeDate>
      <signature>/s/ Audrey Skillern as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Darryl RAWLINGS </signature>
    </noticeSignature>
  </formData>
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</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
