FORM 4 [ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      
1. Name and Address of Reporting Person * Friedman Gavin 2. Issuer Name and Ticker or Trading Symbol TRUPANION, INC. [ TRUP ] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable)_____ Director                    _____ 10% Owner
__X__ Officer (give title below)    _____ Other (specify below)
EVP, People and Legal
(Last)         (First)         (Middle)
6100 4TH AVENUE S, SUITE 200
3. Date of Earliest Transaction (MM/DD/YYYY)
5/25/2021
(Street)
SEATTLE, WA 98108
(City)       (State)       (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)
 
6. Individual or Joint/Group Filing (Check Applicable Line) _X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock  5/25/2021    M    312  A  (1) 853  D   
Common Stock  5/25/2021    F    122 (2) D $83.41  731  D   
Common Stock  5/25/2021    M    684  A  (1) 1415  D   
Common Stock  5/25/2021    F    269 (2) D $83.41  1146  D   
Common Stock  5/25/2021    M    23  A  (1) 1169  D   
Common Stock  5/25/2021    F    9 (2) D $83.41  1160  D   
Common Stock  5/25/2021    M    2746  A  (1) 3906  D   
Common Stock  5/25/2021    F    1080 (2) D $83.41  2826  D   

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Restricted Stock Unit (RSU)   (1) 5/25/2021    M        312    (3) 2/25/2022  Common Stock  312.0  $0  938  D   
Restricted Stock Unit (RSU)   (1) 5/25/2021    M        684    (4) 2/25/2023  Common Stock  684.0  $0  4788  D   
Restricted Stock Unit (RSU)   (1) 5/25/2021    M        23    (5) 11/25/2023  Common Stock  23.0  $0  228  D   
Restricted Stock Unit (RSU)   (1) 5/25/2021    M        2746    (6) 2/25/2024  Common Stock  2746.0  $0  30210  D   

Explanation of Responses:
(1)  Restricted stock units convert into common stock on a one-for-one basis.
(2)  This Form 4 discloses the shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations in connection with the vesting of the restricted stock units, and does not represent a sale by the reporting person.
(3)  The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2019, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.
(4)  The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2020, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.
(5)  The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on November 25, 2020, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.
(6)  The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2021, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
Friedman Gavin
6100 4TH AVENUE S
SUITE 200
SEATTLE, WA 98108


EVP, People and Legal

Signatures
/s/ Charlotte Sim-Warner as attorney-in-fact for Gavin Friedman 5/27/2021
**Signature of Reporting Person Date
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