Darryl Rawlings - 22 May 2025 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role
Director
Signature
/s/ Christina Poler as attorney-in-fact for Darryl Rawlings
Issuer symbol
TRUP
Transactions as of
22 May 2025
Net transactions value
$0
Form type
4
Filing time
27 Aug 2025, 21:54:57 UTC
Previous filing
27 Feb 2025
Next filing
05 Sep 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
RAWLINGS DARRYL Director C/O TRUPANION, INC., 6100 4TH AVENUE SOUTH, SUITE 200, SEATTLE /s/ Christina Poler as attorney-in-fact for Darryl Rawlings 27 Aug 2025 0001611679

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction TRUP Common Stock Options Exercise +6,250 +0.97% 650,621 22 May 2025 Direct F1
transaction TRUP Common Stock Options Exercise +312 +0.05% 650,933 22 May 2025 Direct F1
transaction TRUP Common Stock Options Exercise +945 +0.15% 651,878 22 May 2025 Direct F1
transaction TRUP Common Stock Options Exercise +6,250 +35% 23,956 22 Aug 2025 Direct F1, F2
transaction TRUP Common Stock Options Exercise +313 +1.3% 24,269 22 Aug 2025 Direct F1
transaction TRUP Common Stock Options Exercise +946 +3.9% 25,215 25 Aug 2025 Direct F1
holding TRUP Common Stock 1,463,281 22 May 2025 By Kuyashii Primary Equities LLC F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -6,250 -25% $0.000000 18,750 22 May 2025 Common Stock 6,250 Direct F1, F4
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -312 -8.3% $0.000000 3,438 22 May 2025 Common Stock 312 Direct F1, F5
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -945 -25% $0.000000 2,838 22 May 2025 Common Stock 945 Direct F1, F6
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -6,250 -33% $0.000000 12,500 22 Aug 2025 Common Stock 6,250 Direct F1, F4
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -313 -9.1% $0.000000 3,125 22 Aug 2025 Common Stock 313 Direct F1, F5
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -946 -33% $0.000000 1,892 25 Aug 2025 Common Stock 946 Direct F1, F6
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Restricted stock units convert into common stock on a one-for-one basis.
F2 Gives effect to transfer of 634,172 shares to a limited liability company, indirectly, wholly-owned by the reporting person and reporting person's spouse.
F3 Includes shares described in Footnote (2).
F4 On February 27, 2024, the reporting person was granted 50,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on May 22, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
F5 On February 27, 2024, the reporting person was granted 5,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F6 On February 28, 2022, the Reporting Person was granted 15,132 restricted stock units (RSUs). The RSUs vest and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.