TRUP / Trupanion, Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Trupanion, Inc.
US ˙ NasdaqGM ˙ US8982021060

Mga Batayang Estadistika
LEI 549300J86GFKIDGMQP18
CIK 1371285
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Trupanion, Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
August 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 ☐ TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2025 TRUPANION, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2025 TRUPANION, INC.

August 7, 2025 EX-99.1

Trupanion Reports Second Quarter 2025 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2025 Results SEATTLE, WA. August 7, 2025 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2025. “The second quarter was one of the strongest financial quarters in our history, marked by consistent top-line growth, robust margin expansio

June 17, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 11, 2025 TRUPANION, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 11, 2025 TRUPANION, INC.

May 15, 2025 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 15, 2025 TRUPANION, INC.

May 1, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☑ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Ru

May 1, 2025 EX-10.1

Offer letter, dated August 24, 2023, by and between the Registrant and Fawwad Qureshi.

Exhibit 10.1 August 24, 2023 Fawwad Qureshi Dear Fawwad, We are very pleased to confirm your acceptance of our offer to join Trupanion in the capacity of Chief Financial Officer. You will report to the President with a start date of September 25, 2023. Your salary shall be $25,000.00 per month ($300,000.00 per year). You are also eligible for the following: •An annual bonus of up to 40% of base sa

May 1, 2025 EX-99.1

Trupanion Reports First Quarter 2025 Results

Exhibit 99.1 Trupanion Reports First Quarter 2025 Results SEATTLE, WA. May 1, 2025 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2025. “Q1 was a strong start to the year, with performance ahead of plan across key metrics,” said Margi Tooth, Chief Executive Officer and President of

May 1, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 ☐ TRANSITION REPORT P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

May 1, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 1, 2025 TRUPANION, INC.

April 30, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☑ Filed by a Party o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☑ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Ru

April 30, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitt

February 27, 2025 EX-19

Amended and Restated Insider Trading Policy

TRUPANION, INC. AMENDED AND RESTATED INSIDER TRADING POLICY As amended on February 13, 2025 I.PURPOSE It is illegal for any employee, officer, consultant, contractor, director, or other service provider of Trupanion, Inc. (collectively with its subsidiaries, the “Company”) to trade in the securities of the Company or securities of other publicly traded companies while in the possession of material

February 27, 2025 EX-10.12

Compensation Program for Non-Employee Directors of Trupanion, Inc, as amended on

Compensation Program for Non-Employee Directors of Trupanion, Inc. (As amended through November 8, 2024) 1.Purpose. This Compensation Program for Non-Employee Directors (this “Plan”) is intended to attract highly-qualified individuals to serve as a members of the board of directors (the “Board”) of Trupanion, Inc. (the “Company”) who are not officers or employees of the Company or of any of its su

February 27, 2025 EX-4.1

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2024, Trupanion, Inc. (the “Company”) had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: the Company’s common stock. Description of Capital Stock The following description of the Company’s common

February 27, 2025 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Canada Pet Health Insurance Services, Inc. Canada, Ontario Trupanion Canadian Shareholders Ltd. Canada, Alberta Trupanion Alberta Holding Company, ULC Canada, Alberta Wyndham Insurance Company (SAC), Ltd. - Segregated

February 27, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 19, 2025 EX-99.1

Trupanion Reports Fourth Quarter & Full Year 2024 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter & Full Year 2024 Results SEATTLE, WA. February 19, 2025 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2024. “2024 was a milestone year for Trupanion. Strong execution drove 20% subscription revenue growth, the doublin

February 19, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 19, 2025 TRUPANION, INC.

February 10, 2025 EX-99

JOINT FILING AGREEMENT

JOINT FILING AGREEMENT The undersigned hereby agree that this Schedule 13G (the “Schedule 13G”) with respect to the common stock of TRUPANION, INC.

December 11, 2024 CORRESP

TRUPANION.COM | 855.372.6704 Trupanion is a registered trademark owned by Trupanion, Inc. Underwritten in Canada by Accelerant Insurance Company of Canada, and in the United States by American Pet Insurance Company or ZPIC Insurance Company, 6100 4th

December 11, 2024 via EDGAR Division of Corporation Finance Office of Finance SECURITIES AND EXCHANGE COMMISSION 100 F Street, NE Washington, D.

November 8, 2024 EX-99

JOINT FILING AGREEMENT

EX-99 2 Rule13DJointFilingAgreement.htm JOINT FILING AGREEMENT JOINT FILING AGREEMENT The undersigned hereby agree that this Schedule 13G (the “Schedule 13G”) with respect to the common stock of TRUPANION, INC. is, and any additional amendment thereto signed by each of the undersigned shall be, filed on behalf of each undersigned pursuant to and in accordance with the provisions of 13d-1(k) under

November 8, 2024 SC 13G/A

TRUP / Trupanion, Inc. / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to de

November 1, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

October 30, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 30, 2024 TRUPANION, INC.

October 30, 2024 EX-99.1

Trupanion Reports Third Quarter 2024 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2024 Results SEATTLE, WA. October 30, 2024 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2024. “Q3 was a very strong financial quarter for the company, combining consistent revenue growth with a 66% year-over-year increase in subscr

September 5, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 4, 2024 TRUPANION, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 4, 2024 TRUPANION, INC.

August 9, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 ☐ TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 9, 2024 EX-10.2

Compensation Program for Non-Employee Directors of Trupanion, Inc., as amended on July 30, 2024.

Exhibit 10.2 Compensation Program for Non-Employee Directors of Trupanion, Inc. (As amended through July 30, 2024) 1.Purpose. This Compensation Program for Non-Employee Directors (this “Plan”) is intended to attract highly-qualified individuals to serve as a members of the board of directors (the “Board”) of Trupanion, Inc. (the “Company”) who are not officers or employees of the Company or of any

August 8, 2024 EX-99.1

Trupanion Reports Second Quarter 2024 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2024 Results SEATTLE, WA. August 8, 2024 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2024. “Q2 was a strong quarter, benefitting from consistent revenue growth and margin expansion,” said Margi Tooth, President and Chief Executive

August 8, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2024 TRUPANION, INC.

August 1, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 1, 2024 TRUPANION, INC.

June 7, 2024 S-8

As filed with the Securities and Exchange Commission on June 7, 2024

As filed with the Securities and Exchange Commission on June 7, 2024 Registration No.

June 7, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 5, 2024 TRUPANION, INC.

June 7, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 CALCULATION OF FILING FEE TABLES FORM S-8 (Form Type) TRUPANION, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1)(2) Proposed Maximum Offering Price Per Unit(3) Maximum Aggregate Offering Price(3) Fee Rate Amount of Registration Fee(3) Equity Common Stock, $0.000

June 7, 2024 EX-99.1

2024 Equity Incentive Plan and forms of stock option award agreement, restricted stock agreement and restricted stock unit award agreement thereunder

Exhibit 99.1 TRUPANION, INC. 2024 EQUITY INCENTIVE PLAN 1. PURPOSE. The purpose of this Plan is to provide incentives to attract, retain and motivate eligible persons whose present and potential contributions are important to the success of the Company, and any Parents and Subsidiaries that exist now or in the future, by offering them an opportunity to participate in the Company’s future performan

May 3, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 ☐ TRANSITION REPORT P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

May 2, 2024 EX-99.1

Trupanion Reports First Quarter 2024 Results

Exhibit 99.1 Trupanion Reports First Quarter 2024 Results SEATTLE, WA. May 2, 2024 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2024. “It was a solid start to the year, with performance across our key financial metrics as expected," said Margi Tooth, President of Trupanion. "Su

May 2, 2024 EX-99.2

Trupanion's Margi Tooth Appointed Chief Executive Officer Effective August 1, 2024 –Founder and CEO Darryl Rawlings to continue to serve as Chair of the Board in furtherance of previously announced succession plan

Exhibit 99.2 Trupanion's Margi Tooth Appointed Chief Executive Officer Effective August 1, 2024 –Founder and CEO Darryl Rawlings to continue to serve as Chair of the Board in furtherance of previously announced succession plan SEATTLE, WA. May 2, 2024 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced that its Board of Directors has unanimo

May 2, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 30, 2024 TRUPANION, INC.

April 26, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 26, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 5, 2024 SC 13G/A

TRUP / Trupanion, Inc. / Nielsen Ole - SC 13G/A Passive Investment

SC 13G/A 1 tm2411195d1sc13g.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Trupanion, Inc. (Name of Issuer) Common Stock, par value $0.00001 per share (Title of Class of Securities) 898202106 (CUSIP Number) March 26, 2024 (Date of event which requires filing of this statement) Check the appropriate bo

April 5, 2024 EX-99.2

Amended and Restated Joint Filing Agreement (filed herewith).

EX-99.2 2 tm2411195d1ex99-2.htm EXHIBIT 99.2 Exhibit 99.2 AMENDED AND RESTATED Joint Filing Agreement This Amended and Restated Jointing Filing Agreement amends and restates the Joint Filing Agreement dated November 24, 2023 by and among Ole Nielsen, NCMH ApS and Nielsen Capital Management Fondsmæglerselskab A/S to add Kapitalforeningen Investin Pro – Nielsen Globale Aktier as a party to the Joint

April 4, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 2, 2024 TRUPANION, INC.

February 27, 2024 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Canada Pet Health Insurance Services, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington Trupanion Canadian Shareholders Ltd. Canada, Alberta Trupanion Alber

February 27, 2024 EX-10.10

Addendum #1 to Fronting And Administration Agreement between Omega General Insurance Company and Wyndham Insurance Company (Sac) Limited, effective January 1, 2024.

Exhibit 10.10 ADDENDUM #1 THE FRONTING AND ADMINISTRATION AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Omega") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Wyndham") WHEREAS Omega and Wyndham entered into a Fronting and Administration Agreement effective January 1, 2015 (the "Agreeme

February 27, 2024 EX-10.9

Addendum #11 to Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 2024.

Exhibit 10.9 AGREEMENT NUMBER: 2015003 ADDENDUM #11 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 27, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 27, 2024 EX-4.1

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2023, Trupanion, Inc. (the “Company”) had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: the Company’s common stock. Description of Capital Stock The following description of the Company’s common

February 27, 2024 EX-97.1

Compensation Clawback Policy

Exhibit 97.1 Trupanion Compensation Policies Compensation Clawback Policy Each team member who earns incentive awards, including equity grants, should do so based on an accurate accounting of our performance results and in a way that is consistent with Company policies. Consistent with this objective, the Board of Directors of the Company has established this Clawback Policy, which provides the Co

February 15, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 15, 2024 TRUPANION, INC.

February 15, 2024 EX-99.1

Trupanion Reports Fourth Quarter & Full Year 2023 Results Subscription revenue growth accelerated while margins continued to expand sequentially

Exhibit 99.1 Trupanion Reports Fourth Quarter & Full Year 2023 Results Subscription revenue growth accelerated while margins continued to expand sequentially SEATTLE, WA. February 15, 2024 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2023. The financial result

February 13, 2024 SC 13G/A

TRUP / Trupanion, Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv02119-trupanioninc.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 3)* Name of issuer: Trupanion Inc Title of Class of Securities: Common Stock CUSIP Number: 898202106 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the rul

February 9, 2024 SC 13G/A

TRUP / Trupanion, Inc. / Capital World Investors - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2 )* Trupanion, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

February 8, 2024 SC 13G

TRUP / Trupanion, Inc. / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

SC 13G 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

December 1, 2023 S-3ASR

As filed with the Securities and Exchange Commission on December 1, 2023

As filed with the Securities and Exchange Commission on December 1, 2023 Registration No.

December 1, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table S-3 (Form Type) Trupanion, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered (1) Proposed Maximum Offering Price Per Share (2) Maximum Aggregate Offering Price (2) Fee Rate Amount of Registration Fee

November 24, 2023 EX-99.1

Joint Filing Agreement (filed herewith).

EX-99.1 2 tm2331458d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Joint Filing Agreement In accordance with Rule 13d-1(k)(1) under the Securities Exchange Act of 1934, as amended (the “Act”), each of the undersigned hereby agrees to the joint filing, along with each other such undersigned, on each of its behalf, of a statement of beneficial ownership as required by Sections 13(g) or 13(d) of the Act and t

November 24, 2023 SC 13G

TRUP / Trupanion Inc / Nielsen Ole - SC 13G Passive Investment

    SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549   SCHEDULE 13G   UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )*   Trupanion, Inc. (Name of Issuer)   Common Stock, par value $0.00001 per share (Title of Class of Securities)   898202106 (CUSIP Number)   November 14, 2023 (Date of event which requires filing of this statement)   Check the appropriate box to designate the ru

November 7, 2023 EX-99.1

Trupanion Appoints Richard Enthoven, Global Entrepreneur and Founder of Hollard Insurance Company Australia, as Independent Board Director –A global entrepreneur with decades of experience growing insurance businesses worldwide, including pet insuran

Exhibit 99.1 Trupanion Appoints Richard Enthoven, Global Entrepreneur and Founder of Hollard Insurance Company Australia, as Independent Board Director –A global entrepreneur with decades of experience growing insurance businesses worldwide, including pet insurance brands in Australia and South Africa –Enthoven associated with Tarmac DLTFM LTD., holder of 8.6% of Trupanion outstanding shares SEATT

November 7, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 2, 2023 TRUPANION, INC.

November 3, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

November 2, 2023 EX-99.1

Trupanion Reports Third Quarter 2023 Results Trupanion returns to positive cash flow as margins continue to expand

Exhibit 99.1 Trupanion Reports Third Quarter 2023 Results Trupanion returns to positive cash flow as margins continue to expand SEATTLE, WA. November 2, 2023 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2023. “I am happy to report we achieved $11 million in operating cash f

November 2, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 2, 2023 TRUPANION, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 2, 2023 TRUPANION, INC.

September 21, 2023 SC 13G

TRUP / Trupanion Inc / Tarmac DLTFM Ltd - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* TRUPANION, INC (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 898202106 (CUSIP Number) September 14, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule p

September 6, 2023 EX-99.1

Trupanion Announces Appointment of Fawwad Qureshi as Chief Financial Officer - A senior financial leader for over two decades, Qureshi brings a wealth of experience driving growth and profitability for publicly-traded, global growth organizations -

Exhibit 99.1 Trupanion Announces Appointment of Fawwad Qureshi as Chief Financial Officer - A senior financial leader for over two decades, Qureshi brings a wealth of experience driving growth and profitability for publicly-traded, global growth organizations - Seattle, WA – September 6, 2023 – Trupanion, Inc. (Nasdaq: TRUP), the leading provider of pet medical insurance for cats and dogs, announc

September 6, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 2, 2023 TRUPANION, INC.

September 6, 2023 EX-10.1

Offer Letter dated as of August 24, 2023, by and between the Company and Fawwad Qureshi.

Exhibit 10.1 August 24, 2023 Fawwad Qureshi 15435 SW Brighton Way Beaverton, OR 97007 Dear Fawwad, We are very pleased to confirm your acceptance of our offer to join Trupanion in the capacity of Chief Financial Officer. You will report to the President with a start date of September 25, 2023. Your salary shall be $25,000.00 per month ($300,000.00 per year). You are also eligible for the following

August 4, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 ☐ TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 4, 2023 EX-10.2

Trupanion, Inc. Severance and Change in Control Plan effective July 28, 2023.

Exhibit 10.2 TRUPANION, INC. EMPLOYEE SEVERANCE AND CHANGE IN CONTROL PLAN ARTICLE I PURPOSE This Employee Severance and Change in Control Plan (the “Plan”) has been established by the Company on January 29, 2021 (the “Effective Date”) and amended as of July 28, 2023 to provide Participants with the opportunity to receive severance benefits in the event of certain terminations of employment and pr

August 4, 2023 EX-10.1

Compensation Program for Non-Employee Directors of Trupanion, Inc, as amended on April 21, 2023.

Exhibit 10.1 Compensation Program for Non-Employee Directors of Trupanion, Inc. (As amended through April 21, 2023) 1. Purpose. This Compensation Program for Non-Employee Directors (this “Plan”) is intended to attract highly-qualified individuals to serve as a members of the board of directors (the “Board”) of Trupanion, Inc. (the “Company”) who are not officers or employees of the Company or of a

August 3, 2023 EX-99.1

Trupanion Reports Second Quarter 2023 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2023 Results SEATTLE, WA. August 3, 2023 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2023. “In the second quarter, we saw early signs of margin expansion while exercising discipline in our capital deployment. As a result, we delive

August 3, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 3, 2023 TRUPANION, INC.

July 5, 2023 EX-99.1

Trupanion Appoints Aflac Incorporated CFO Max Brodén to Board of Directors –Mr. Brodén Brings Global Financial Acumen and Continues Ongoing Refreshment of Board

Exhibit 99.1 Trupanion Appoints Aflac Incorporated CFO Max Brodén to Board of Directors –Mr. Brodén Brings Global Financial Acumen and Continues Ongoing Refreshment of Board SEATTLE, WA. July 5, 2023 - Trupanion, Inc. (Nasdaq: TRUP) announced that Max Brodén, Chief Financial Officer of Aflac Incorporated, has been appointed to serve as an independent director effective July 4, 2023. This appointme

July 5, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 3, 2023 TRUPANION, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 3, 2023 TRUPANION, INC.

June 12, 2023 EX-3.1

Amended and Restated Certificate of Incorporation of Trupanion, Inc.

Exhibit 3.1 TRUPANION, INC. AMENDED AND RESTATED CERTIFICATE OF INCORPORATION Trupanion, Inc., a Delaware corporation, hereby certifies as follows. 1. The name of the corporation is Trupanion, Inc. The date of filing its original Certificate of Incorporation with the Secretary of State was April 4, 2006, under the name Vetinsurance International, Inc. 2. The Amended and Restated Certificate of Inc

June 12, 2023 EX-3.3

TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS As Adopted January June 829, 20213 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Article I - STOCKHOLDERS Section 1.1: Annual Meetings Section 1

Exhibit 3.3 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS As Adopted January June 829, 20213 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Article I - STOCKHOLDERS Section 1.1: Annual Meetings Section 1.2: Special Meetings Section 1.3: Notice of Meetings Section 1.4: Adjournments Section 1.5: Quorum Section 1.6: Organization Section 1.7:

June 12, 2023 EX-3.2

Amended and Restated Bylaws of Trupanion, Inc.

Exhibit 3.2 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS As Adopted June 8, 2023 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Article I - STOCKHOLDERS Section 1.1: Annual Meetings Section 1.2: Special Meetings Section 1.3: Notice of Meetings Section 1.4: Adjournments Section 1.5: Quorum Section 1.6: Organization Section 1.7: Voting; Pro

June 12, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 7, 2023 TRUPANION, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 7, 2023 TRUPANION, INC.

May 5, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 ☐ TRANSITION REPORT P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

May 4, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 4, 2023 TRUPANION, INC.

May 4, 2023 EX-99.1

Trupanion Reports First Quarter 2023 Results

Exhibit 99.1 Trupanion Reports First Quarter 2023 Results SEATTLE, WA. May 4, 2023 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2023. “In Q1, veterinary inflation increased 15% year-over-year, approximately 3% higher than our assumptions,” said Darryl Rawlings, Trupanion's foun

April 28, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEFA14A 1 defa14ainternetavailabilit.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, f

April 28, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 27, 2023 EX-99.1

Trupanion Appoints Paulette Dodson and Betsy McLaughlin to Board of Directors –New Independent Directors Bring Significant Experience with Global Growth Brands

Exhibit 99.1 Trupanion Appoints Paulette Dodson and Betsy McLaughlin to Board of Directors –New Independent Directors Bring Significant Experience with Global Growth Brands SEATTLE, WA. April 27, 2023 - Trupanion, Inc. (Nasdaq: TRUP) announced today the appointment of Paulette Dodson, former General Counsel and Corporate Secretary at Alight, Inc., PetSmart Inc., and Sara Lee Corporation, and Eliza

April 27, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 21, 2023 TRUPANION, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 21, 2023 TRUPANION, INC.

April 27, 2023 EX-99.2

Contingent Resignation Solely to End Staggered Terms

Exhibit 99.2 Contingent Resignation Solely to End Staggered Terms The undersigned member of the Board of Directors (the “Board”) of Trupanion, Inc. (the “Company”) director hereby resigns, contingent and effective upon: 1.In the case of Class I and Class II directors, (a) the approval by stockholders, filing, and effectiveness of the Company’s amended and restated certificate of incorporation to d

April 17, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 11, 2023 TRUPANION, INC.

April 17, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: þ Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 4, 2023 EX-10.1

Form of Consulting Agreement.

Exhibit 10.1 [Date] Trupanion, Inc. 6100 4th Avenue S, Suite 400 Seattle, Washington 98108 VIA ELECTRONIC MAIL [Executive Officer] [Address] RE: Consulting Agreement Dear [Name], This letter agreement (this “Agreement”) sets forth the terms and conditions whereby you agree to provide certain services (as described on Schedule 1) to Trupanion Managers USA, Inc., an Arizona corporation (the “Company

April 4, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 29, 2023 TRUPANION, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 29, 2023 TRUPANION, INC.

April 4, 2023 EX-10.2

Form of Separation Agreement.

Exhibit 10.2 CONFIDENTIAL SEPARATION AGREEMENT AND GENERAL RELEASE OF ALL CLAIMS This Confidential Separation Agreement and General Release of All Claims (“Agreement”) is made by and between Trupanion Managers USA, Inc. (“Company”) and [Executive Officer] (“Team Member”) effective as of [Date] with respect to the following facts: A. Team Member has been employed by Company since [Date]. B. Team Me

March 23, 2023 EX-99.1

Trupanion Announces Executive Leadership Transitions

Exhibit 99.1 Trupanion Announces Executive Leadership Transitions Seattle, WA - March 23, 2023 - Trupanion, Inc. (Nasdaq: TRUP) today announced the following changes to its executive leadership team: •Drew Wolff, Chief Financial Officer, will be stepping down from his position effective June 1, 2023. Thereafter, Mr. Wolff will serve as a senior advisor to the Company to support the Interim CFO, an

March 23, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 22, 2023 TRUPANION, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 22, 2023 TRUPANION, INC.

February 16, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 16, 2023 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Canada Pet Health Insurance Services, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington Trupanion Canadian Shareholders Ltd. Canada, Alberta Trupanion Alber

February 16, 2023 EX-10.9

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 2023.

Exhibit 10.9 AGREEMENT NUMBER: 2015003 ADDENDUM #10 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 15, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 15, 2023 TRUPANION, INC.

February 15, 2023 EX-99.1

Trupanion Reports Fourth Quarter and Full Year 2022 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter and Full Year 2022 Results SEATTLE, WA. February 15, 2023 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2022. “2022 was another year of consistent revenue growth and we set solid foundations for our long-term growth

February 13, 2023 SC 13G/A

TRUP / Trupanion Inc / Capital World Investors - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Trupanion, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

February 10, 2023 SC 13G

TRUP / Trupanion Inc / FLOSSBACH VON STORCH AG Passive Investment

SC 13G 1 d994385813g.htm SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b)(c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(b) (Amendment No.) TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2022 (Date of Event

February 9, 2023 SC 13G/A

TRUP / Trupanion Inc / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv02087-trupanioninc.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 2)* Name of issuer: Trupanion Inc. Title of Class of Securities: Common Stock CUSIP Number: 898202106 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate the ru

February 6, 2023 SC 13G/A

TRUP / Trupanion Inc / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4 )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to des

January 10, 2023 EX-99.1

Trupanion Founder & CEO Darryl Rawlings to Assume Additional Role of Chair of the Board –Company to Propose Declassification of Board

Exhibit 99.1 Trupanion Founder & CEO Darryl Rawlings to Assume Additional Role of Chair of the Board –Company to Propose Declassification of Board SEATTLE, WA. January 10, 2022 - Trupanion, Inc. (Nasdaq: TRUP) announced today that Darryl Rawlings, Founder & Chief Executive Officer, will assume the additional role of Chair of the Board, effective immediately. Murray Low, PhD, the prior Chair of the

January 10, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 10, 2023 TRUPANION, INC.

November 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

November 3, 2022 EX-99.3

Trupanion Signs Agreement to Acquire PetExpert, Continuing European Expansion

Exhibit 99.3 Trupanion Signs Agreement to Acquire PetExpert, Continuing European Expansion SEATTLE, WA. November 3, 2022 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, announced today the signing of a definitive agreement to acquire Royal Blue s.r.o, the parent company of PetExpert, a veterinary-centric, pet insurance provider with tens of thousands

November 3, 2022 EX-99.1

Trupanion Reports Third Quarter 2022 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2022 Results SEATTLE, WA. November 3, 2022 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2022. ?The team's ability to deploy capital at strong estimated internal rates of return continues to impress. This is illustrated by our rec

November 3, 2022 EX-99.2

1

Exhibit 99.2 November 1, 2022 Gavin Friedman, Corporate Secretary Trupanion, Inc. 6100 4th Avenue South, Suite 200 Seattle, Washington 98107 Dear Mr. Friedman, In accordance with the Trupanion, Inc. (the "Company") Director Resignation Policy, I hereby tender my resignation as a member of the board of directors of the Company, effective as of January 1, 2023. Please note that my resignation is not

November 3, 2022 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 1, 2022 TRUPANION, INC.

August 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 ☐ TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 3, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 3, 2022 TRUPANION, INC.

August 3, 2022 EX-99.1

Trupanion Reports Second Quarter 2022 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2022 Results SEATTLE, WA. August 3, 2022 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2022. ?Revenue growth was consistent in the quarter and we saw a modest increase in our profit from existing pets before investing in growth,? sai

June 13, 2022 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 8, 2022 TRUPANION, INC.

April 29, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

April 29, 2022 EX-10.2

Compensation Program for Non-Employee Directors of Trupanion, Inc, as amended on February 22, 2022.

Exhibit 10.2 Compensation Program for Non-Employee Directors of Trupanion, Inc. (Adopted on February 6, 2018, amended on September 5, 2018, on December 27, 2018, and on April 17, 2020, and amended and restated on January 29, 2021, and on February 22, 2022) 1. Purpose. This Compensation Program for Non-Employee Directors (this ?Plan?) is intended to attract highly-qualified individuals to serve as

April 29, 2022 EX-10.1

Credit Agreement, dated as of March 25, 2022, by and among Trupanion, Inc., Piper Sandler Finance, LLC, as administrative agent, and the lenders party thereto.

Exhibit 10.1 CERTAIN PORTIONS OF THIS EXHIBIT HAVE BEEN EXCLUDED, AS MARKED WITH BRACKETS (?[****]?), BECAUSE SUCH PORTIONS ARE NOT MATERIAL AND ARE THE TYPE OF INFORMATION THAT THE REGISTRANTS TREATS AS PRIVATE OR CONFIDENTIAL. CREDIT AGREEMENT dated as of March 25, 2022, among TRUPANION, INC. as Borrower, THE LENDERS PARTY HERETO, and PIPER SANDLER FINANCE, LLC, as Administrative Agent TABLE OF

April 28, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 28, 2022 TRUPANION, INC.

April 28, 2022 EX-99.1

Trupanion Reports First Quarter 2022 Results

Exhibit 99.1 Trupanion Reports First Quarter 2022 Results SEATTLE, WA. April 28, 2022 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2022. ?Q1 was a solid growth quarter, benefiting from another quarter of record pet additions and consistently strong levels of retention in our su

April 26, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEF 14A 1 def14a-proxystatement2022.htm DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, fo

April 26, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 28, 2022 8-K

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 25, 2022 TRUPANION, INC.

February 17, 2022 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Canada Pet Health Insurance Services, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington Trupanion Canadian Shareholders Ltd. Canada, Alberta Trupanion Alber

February 17, 2022 EX-10.10

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 202

Exhibit 10.10 AGREEMENT NUMBER: 2015003 ADDENDUM #9 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 17, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 16, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 10, 2022 TRUPANION, INC.

February 16, 2022 EX-99.1

Trupanion Reports Fourth Quarter and Full Year 2021 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter and Full Year 2021 Results SEATTLE, WA. February 16, 2022 - Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2021. ?Our 60 month plan is off to a great start, as shown in our strong year-over-year growth metrics,? said D

February 11, 2022 SC 13G

TRUP / Trupanion Inc / Capital World Investors - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Trupanion, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule

February 10, 2022 SC 13G/A

TRUP / Trupanion Inc / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 1)* Name of issuer: Trupanion Inc. Title of Class of Securities: Common Stock CUSIP Number: 898202106 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to which this Schedule is filed: ??Rule

February 4, 2022 SC 13G/A

TRUP / Trupanion Inc / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3 )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

November 4, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

November 3, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 3, 2021 TRUPANION, INC.

November 3, 2021 EX-99.1

Trupanion Reports Third Quarter 2021 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2021 Results SEATTLE, WA. November 3, 2021- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2021. ?Q3 marks the continuation of our strong momentum, as shown in our key financial measures. We continue to grow the funds available to us

September 29, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 24, 2021 TRUPANION, INC.

September 29, 2021 EX-99.1

Trupanion Promotes Drew Wolff to Chief Financial Officer

Exhibit 99.1 Trupanion Promotes Drew Wolff to Chief Financial Officer Seattle, WA - September 29, 2021- Trupanion, Inc. (Nasdaq: TRUP) announced today the promotion of Drew Wolff to Executive VP and Chief Financial Officer, effective October 1, 2021. Tricia Plouf, Trupanion?s current CFO, will remain in the position of Co-President, overseeing the Company?s finance, actuarial, people and legal, te

August 6, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ☐ TRANSITION REPORT PU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 5, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 30, 2021 TRUPANION, INC.

August 5, 2021 EX-99.1

Trupanion Reports Second Quarter 2021 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2021 Results SEATTLE, WA. August 5, 2021- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2021. ?Q2 was another great quarter with net pet growth up 60% year-over-year, led by exceptionally strong retention rates,? said Darryl Rawlings,

June 17, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 16, 2021 TRUPANION, INC.

June 10, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 30, 2021 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

April 29, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 29, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 29, 2021 TRUPANION, INC.

April 29, 2021 EX-99.1

Trupanion Reports First Quarter 2021 Results

Exhibit 99.1 Trupanion Reports First Quarter 2021 Results SEATTLE, WA. April 29, 2021- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2021. ?2021 is off to a flying start, with revenues up 39% year-over-year, led by growth in subscription pets,? said Darryl Rawlings, founder and ch

April 29, 2021 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 15, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5)* Trupanion Inc. (Name of Issuer) Common Stock (Title of Class of Securities) (CUSIP Number) March 31, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5)* Trupanion Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) March 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is

March 4, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 1, 2021 TRUPANION, INC.

February 16, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5 )* Trupanion, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

February 12, 2021 EX-10.17

Compensation Program for Non-Employee Directors of Trupanion, Inc, as amended on January 29, 2021.

Exhibit 10.17 Compensation Program for Non-Employee Directors of Trupanion, Inc. (Adopted on February 6, 2018, amended on September 5, 2018, on December 27, 2018, and on April 17, 2020, and amended and restated on January 29, 2021) 1. Purpose. This Compensation Program for Non-Employee Directors (this ?Plan?) is intended to attract highly-qualified individuals to serve as a members of the board of

February 12, 2021 EX-3.3

Amended and Restated Bylaws of the Registrant.

Exhibit 3.3 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS As Adopted January 29, 2021 - 1 - TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Article I - STOCKHOLDERS Section 1.1: Annual Meetings Section 1.2: Special Meetings Section 1.3: Notice of Meetings Section 1.4: Adjournments Section 1.5: Quorum Section 1.6: Organization Section 1.7: V

February 12, 2021 EX-10.16

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 2021.

Exhibit 10.16 AGREEMENT NUMBER: 2015003 ADDENDUM #8 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 12, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 12, 2021 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Canada Pet Health Insurance Services, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington Trupanion Canadian Shareholders Ltd. Canada, Alberta North American

February 10, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Trupanion Inc. Title of Class of Securities: Common Stock CUSIP Number: 898202106 Date of Event Which Requires Filing of this Statement: December 31, 2020 Check the appropriate box to designate the rule pursuant to which this Schedule is filed: ☒ Rule 13d-1(b) ☐ Rule 13d

February 10, 2021 EX-99.1

Trupanion Reports Fourth Quarter and Full Year 2020 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter and Full Year 2020 Results SEATTLE, WA. February 10, 2021- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2020. “The fourth quarter capped off a strong year for Trupanion. We’re set up well to capture the growing oppor

February 10, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 10, 2021 TRUPANION, INC.

February 8, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2 )* Trupanion Inc (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule

February 4, 2021 EX-3.1

Exhibit 3.1

Exhibit 3.1 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS As Adopted July 23January 29, 20142021 TRUPANION, INC. a Delaware Corporation AMENDED AND RESTATED BYLAWS TABLE OF CONTENTS Article I - STOCKHOLDERS Section 1.1: Annual Meetings Section 1.2: Special Meetings Section 1.3: Notice of Meetings Section 1.4: Adjournments Section 1.5: Quorum Section 1.6: Organization Section 1

February 4, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 29, 2021 TRUPANION, INC.

February 4, 2021 EX-10.1

Trupanion, Inc. Employee Severance and Change in Control Plan effective January 29, 2021.

Exhibit 10.1 Trupanion, Inc. EMPLOYEE Severance and change in control Plan ARTICLE I Purpose This Employee Severance and Change in Control Plan (the “Plan”) has been established by the Company on January 29, 2021 (the “Effective Date”) to provide Participants with the opportunity to receive severance benefits in the event of certain terminations of employment and provide Participants with the oppo

February 4, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2 )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

January 5, 2021 8-K

Termination of a Material Definitive Agreement - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 29, 2020 TRUPANION, INC.

December 1, 2020 S-3ASR

- S-3ASR

As filed with the Securities and Exchange Commission on December 1, 2020 Registration No.

December 1, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 25, 2020 TRUPANION, INC.

November 20, 2020 SC 13G

TRUP / Trupanion, Inc. / AFLAC INC - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.

November 13, 2020 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 13, 2020 TRUPANION, INC.

October 30, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

October 29, 2020 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 26, 2020 TRUPANION, INC.

October 29, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 29, 2020 TRUPANION, INC.

October 29, 2020 EX-99.1

1

Exhibit 99.1 Aflac and Trupanion Announce Distribution Alliance and Investment COLUMBUS, Ga., SEATTLE October 29, 2020 /PRNewswire/- Aflac Incorporated (NYSE: AFL), a Fortune 200 company that helps provide protection to more than 50 million people in Japan and the U.S., and Trupanion, Inc. (Nasdaq: TRUP), a leader in medical insurance for cats and dogs, are pleased to have entered into an exclusiv

October 29, 2020 EX-10.1

Stock Purchase Agreement, dated as of October 26, 2020 by and between Trupanion, Inc. and Aflac Incorporated.

Exhibit 10.1 STOCK PURCHASE AGREEMENT between TRUPANION, INC. and AFLAC INCORPORATED dated as of October 26, 2020 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS Section 1.01 Definitions 1 Section 1.02 Interpretation 6 ARTICLE II AGREEMENT TO SELL AND PURCHASE Section 2.01 Sale and Purchase 6 Section 2.02 Closings 7 Section 2.03 Mutual Conditions to Each Party's Obligations 7 Section 2.04 Conditions

October 29, 2020 EX-10.3

Shareholder Agreement, dated as of October 26, 2020 by and between Trupanion, Inc. and Aflac Incorporated.

Exhibit 10.3 SHAREHOLDER AGREEMENT by and between TRUPANION, INC. and AFLAC INCORPORATED Dated as of October 26, 2020 Table of Contents Page ARTICLE I DEFINITIONS 1 Section 1.1 Definitions 1 Section 1.2 Additional Defined Terms 3 Section 1.3 Interpretation and Construction 4 ARTICLE II STANDSTILL 5 Section 2.1 Standstill 5 ARTICLE III PREEMPTIVE RIGHTS 7 Section 3.1 Preemptive Rights 7 ARTICLE IV

October 29, 2020 EX-10.2

Strategic Alliance Agreement, dated as of October 26, 2020 by and between Trupanion, Inc. and Aflac Incorporated.

Exhibit 10.2 Strategic Alliance Agreement This Strategic Alliance Agreement (this “Agreement”), dated as of October 26, 2020, is entered into by and between Aflac Incorporated (“Aflac”) and Trupanion, Inc. (“Trupanion”) (each, a “Party” and, collectively, the “Parties”). WHEREAS, pet insurance is a growing, but underpenetrated market in the United States; WHEREAS, pet insurance industry revenue gr

October 29, 2020 EX-99.1

Trupanion Reports Third Quarter 2020 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2020 Results SEATTLE, WA. October 29, 2020- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2020. “It was another strong quarter for Trupanion, with high retention rates driving accelerated growth in net subscription pets,” said Darry

August 5, 2020 EX-10.1

Sixth Amendment to Senior Credit Facility Loan and Security Agreement, dated April 28, 2020 between Pacific Western Bank, Western Alliance Bank and the Registrant.

Exhibit 10.1 SIXTH AMENDMENT TO LOAN AND SECURITY AGREEMENT This SIXTH AMENDMENT TO LOAN AND SECURITY Agreement (this “Amendment”) is entered into as of April 28, 2020, by and among TRUPANION, INC., a Delaware corporation (“Trupanion”), TRUPANION MANAGERS USA, INC., an Arizona corporation (“Trupanion Managers”), and 6100 BUILDING, LLC (formerly known as Trupanion-APIC, LLC), a Washington limited l

August 5, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 4, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 4, 2020 TRUPANION, INC.

August 4, 2020 EX-99.1

Trupanion Reports Second Quarter 2020 Results

EX-99.1 2 ex991q22020.htm EX-99.1 Exhibit 99.1 Trupanion Reports Second Quarter 2020 Results SEATTLE, WA. August 4, 2020- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2020. “Across key financial and operational metrics, it was a very strong quarter for Trupanion,” said Darryl Raw

June 16, 2020 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 11, 2020 TRUPANION, INC.

June 8, 2020 DEFA14A

- DEFA 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

May 1, 2020 EX-10.1

Fifth Amendment to Senior Credit Facility Loan and Security Agreement, dated February 27, 2020 between Pacific Western Bank, Western Alliance Bank and the Registrant.

Exhibit 10.1 FIFTH AMENDMENT TO LOAN AND SECURITY AGREEMENT This FIFTH AMENDMENT TO LOAN AND SECURITY Agreement (this “Amendment”) is entered into as of February 27, 2020, by and among TRUPANION, INC., a Delaware corporation (“Trupanion”), TRUPANION MANAGERS USA, INC., an Arizona corporation (“Trupanion Managers”), and 6100 BUILDING, LLC (formerly known as Trupanion-APIC, LLC), a Washington limite

May 1, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

April 30, 2020 EX-99.1

Trupanion Reports First Quarter 2020 Results

Exhibit 99.1 Trupanion Reports First Quarter 2020 Results SEATTLE, WA. April 30, 2020- Trupanion, Inc. (Nasdaq: TRUP), the leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2020. “At Trupanion, we understand the power of the pet,” said Darryl Rawlings, Founder and CEO of Trupanion. “In times of uncertainty, heightened a

April 30, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 30, 2020 TRUPANION, INC.

April 28, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 28, 2020 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

February 18, 2020 SC 13G/A

TRUP / Trupanion, Inc. / ALLIANCEBERNSTEIN L.P. - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Trupanion Inc (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule

February 14, 2020 SC 13G/A

TRUP / Trupanion, Inc. / RAWLINGS DARRYL - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Amendment No. 5) Under the Securities Exchange Act of 1934 Trupanion, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule p

February 14, 2020 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Trupanion Brokers Ontario, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington Trupanion Canadian Shareholders Ltd. Canada, Alberta North American Pet Insuran

February 14, 2020 EX-10.22

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 2020.

Exhibit 10.22 AGREEMENT NUMBER: 2015003 ADDENDUM #6 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 14, 2020 EX-10.23

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective July 1, 2020.

Exhibit 10.23 AGREEMENT NUMBER: 2015003 ADDENDUM #7 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effec

February 14, 2020 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 14, 2020 EX-4.1

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2019, Trupanion, Inc. (the “Company”) had one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: the Company’s common stock. Description of Capital Stock The following description of the Company’s common

February 13, 2020 EX-99.1

Trupanion Reports Fourth Quarter and Full Year 2019 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter and Full Year 2019 Results SEATTLE, WA. February 13, 2020 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and year ended December 31, 2019. “Over the past two decades, we’ve delivered consistent growth while scaling our operating expenses,” said Darryl

February 13, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2020 TRUPANION, INC.

January 8, 2020 SC 13G/A

TRUP / Trupanion, Inc. / Wellington Management Group LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

November 6, 2019 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

November 5, 2019 EX-99.1

Trupanion Reports Third Quarter 2019 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2019 Results SEATTLE, WA. November 5, 2019 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2019. “Performance in the third quarter was strong. Our subscription business benefitted from a double digit increase in lead volume and strong

November 5, 2019 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 5, 2019 TRUPANION, INC.

July 31, 2019 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

July 31, 2019 EX-10.1

Fourth Amendment to Senior Credit Facility Loan and Security Agreement, dated April 29, 2019 between Pacific Western Bank, Western Alliance Bank and the Registrant.

Exhibit 10.1 FOURTH AMENDMENT TO LOAN AND SECURITY AGREEMENT THIS FOURTH Amendment to Loan and Security Agreement (this “Amendment”), is entered into as of April 29, 2019, by and among TRUPANION, INC., a Delaware corporation (“Trupanion”), TRUPANION MANAGERS USA, INC., an Arizona corporation (“Trupanion Managers”), and 6100 BUILDING, LLC (formerly known as Trupanion-APIC, LLC), a Washington limite

July 30, 2019 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 30, 2019 TRUPANION, INC.

July 30, 2019 EX-99.1

Trupanion Reports Second Quarter 2019 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2019 Results SEATTLE, WA. July 30, 2019 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2019. “It was another consistent quarter, with solid growth in revenue and scaling fixed expenses translating into greater investable funds,” said Da

June 12, 2019 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 6, 2019 TRUPANION, INC.

June 10, 2019 CORRESP

TRUP / Trupanion, Inc. CORRESP - -

June 10, 2019 via EDGAR Division of Corporation Finance Office of Healthcare & Insurance SECURITIES AND EXCHANGE COMMISION 100 F Street, NE Washington, D.

May 15, 2019 CORRESP

TRUP / Trupanion, Inc. CORRESP - -

May 15, 2019 via EDGAR Division of Corporation Finance Office of Healthcare & Insurance SECURITIES AND EXCHANGE COMMISION 100 F Street, NE Washington, D.

May 3, 2019 EX-10.2

Third Amendment to Consulting Agreement, dated January 1, 2019 by and between the Registrant and Howard Rubin.

Exhibit 10.2 THIRD AMENDMENT TO CONSULTING AGREEMENT This Third Amendment to Consulting Agreement (as amended from time to time, this “Amendment”) is effective as of January 1, 2019 (the “Effective Date”), by and among Trupanion Managers USA, Inc., an Arizona corporation (the “Company”) and Howard Rubin, an independent contractor of the Company (“You” or “Rubin”, and together with the Company, the

May 3, 2019 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION

May 2, 2019 EX-99.1

Trupanion Reports First Quarter 2019 Results

Exhibit 99.1 Trupanion Reports First Quarter 2019 Results SEATTLE, WA. May 2, 2019 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the first quarter ended March 31, 2019. “We executed consistently across our business in the first quarter,” said Darryl Rawlings, Founder and CEO of Trupanion. “We invested more capital

May 2, 2019 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 29, 2019 TRUPANION, INC.

April 26, 2019 DEFA14A

TRUP / Trupanion, Inc. DEFA14A DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 26, 2019 DEF 14A

TRUP / Trupanion, Inc. DEF 14A DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

February 14, 2019 EX-10.21

Compensation Clawback Policy, effective February 11, 2019.

Exhibit 10.21 Trupanion Compensation Policies Compensation Clawback Policy Each team member who earns incentive awards, including equity grants, should do so based on an accurate accounting of our performance results and in a way that is consistent with Company policies. Consistent with this objective, the Compensation Committee has established this Clawback Policy, which provides the Compensation

February 14, 2019 EX-21.1

Subsidiaries of the Registrant.

Exhibit 21.1 Trupanion, Inc. List of Subsidiaries Subsidiary Incorporation American Pet Insurance Company United States, New York Trupanion Managers USA, Inc. United States, Arizona Trupanion Brokers Ontario, Inc. Canada, Ontario Wyndham Insurance Company (SAC), Ltd. Bermuda 6100 Building, LLC United States, Washington

February 14, 2019 EX-10.23

Change of Control Policy for Select Officers and Key Leaders effective February 11, 2019.

Exhibit 10.23 Trupanion Compensation Policies Change of Control Policy for Select Officers and Key Leaders In a situation where there is a Change of Control of Trupanion, certain “covered” executives may leave involuntarily (termination without cause). A Change of Control Severance policy provides a fair framework for these covered terminations if the termination event occurs within 6 months prior

February 14, 2019 SC 13G/A

TRUP / Trupanion, Inc. / RenaissanceRe Ventures Ltd. - SCHEDULE 13G/A, #4 Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4)* Trupanion Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule

February 14, 2019 EX-10.22

On-Going Severance Policy for CEO and Key Senior Leaders, effective February 11, 2019.

Exhibit 10.22 Trupanion Compensation Policies On-Going Severance Policy for CEO and Key Senior Leaders This Severance Policy creates a fair framework for situations when a covered executive leaves the Company involuntarily (termination without cause). The roles that this policy covers are included in the Appendix A and may change from time to time. The catalog of covered and non-covered terminatio

February 14, 2019 EX-10.20

Compensation Program for Non-Employee Directors of Trupanion, Inc, as amended on December 27, 2018.

Exhibit 10.20 Compensation Program for Non-Employee Directors of Trupanion, Inc. (the “Company”) (Adopted on February 6, 2018, as amended on September 5, 2018, and on December 27, 2018) Compensation. 1. Value of Compensation (“Award Values”) a. Non-Employee Board of Director Compensation: i. Annual value of compensation for all Non-Employee Board of Directors (“Board”) members: $75,000 b. Addition

February 14, 2019 SC 13G/A

TRUP / Trupanion, Inc. / RAWLINGS DARRYL - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Amendment No. 4) Under the Securities Exchange Act of 1934 Trupanion, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule p

February 14, 2019 EX-10.19

Quota Share Reinsurance Agreement between Wyndham Insurance Company (SAC) Limited and Omega General Insurance Company, effective January 1, 2019.

Exhibit 10.19 AGREEMENT NUMBER: 2015003 ADDENDUM#5 QUOTA SHARE REINSURANCE AGREEMENT made between OMEGA GENERAL INSURANCE COMPANY (hereinafter referred to as the "Reinsured") and WYNDHAM INSURANCE COMPANY (SAC) LIMITED, in respect of its Segregated Account AX (hereinafter referred to as the "Reinsurer") WHEREAS the Reinsured and the Reinsurer entered into a Quota Share Reinsurance Agreement effect

February 14, 2019 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION, INC

February 13, 2019 EX-99.1

Trupanion Reports Fourth Quarter and Full Year 2018 Results

Exhibit 99.1 Trupanion Reports Fourth Quarter and Full Year 2018 Results SEATTLE, WA. February 13, 2019 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the fourth quarter and full year ended December 31, 2018. “2018 was another year of steady growth and progress at Trupanion. We grew revenue by 25% year-over-year, e

February 13, 2019 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2019 TRUPANION, INC.

February 13, 2019 SC 13G

TRUP / Trupanion, Inc. / ALLIANCEBERNSTEIN L.P. - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Trupanion Inc (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule i

February 13, 2019 EX-99.2

RESIGNATION LETTER

Exhibit 99.2 RESIGNATION LETTER February 13, 2019 Corporate Secretary Trupanion, Inc. 6100 4th Avenue South, Suite 200 Seattle, Washington 98107 Dear Trupanion Corporate Secretary: In accordance with the Trupanion, Inc. Director Resignation Policy, I hereby: o Tender my resignation as a member of the board of directors of Trupanion, Inc., effective as of x Refuse to stand for re-election to the bo

February 12, 2019 SC 13G

TRUP / Trupanion, Inc. / Wellington Management Group LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* TRUPANION, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule

February 7, 2019 SC 13G/A

TRUP / Trupanion, Inc. / Maveron Equity Partners III, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No. 4)* Trupanion, Inc. (Name of Issuer) Common Stock Par Value $0.00001 (Title of Class of Securities) 898202106 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sc

November 9, 2018 EX-10.1

Amended Compensation Program for Non-Employee Directors of Trupanion, Inc. dated September 5, 2018

Exhibit 10.1 Compensation Program for Non-Employee Directors of Trupanion, Inc. (the “Company”) (Adopted on February 6, 2018, as amended on September 5, 2018) Compensation. 1. Value of Compensation (“Award Values”) a. Non-Employee Board of Director Compensation: i. Annual value of compensation for all Non-Employee Board of Directors (“Board”) members: $75,000 b. Additional Committee Compensation (

November 9, 2018 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPA

November 9, 2018 EX-10.2

Joinder to Loan and Security Agreement and Amendment and Restated Revolving Note, dated August 6, 2018, between Pacific Western Bank, Western Alliance Bank, Trupanion Managers USA, Inc. and Trupanion-APIC, LLC.

Exhibit 10.2 JOINDER TO LOAN AND SECURITY AGREEMENT This Joinder to Loan and Security Agreement (this “Joinder”), dated as of August 6, 2018 (the “Effective Date”), is executed and delivered by and among TRUPANION-APIC, LLC, a Washington limited liability company (“New Borrower”), the several banks and other financial institutions or entities from time to time party to the Agreement (as hereinafte

November 8, 2018 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2018 TRUPANION, INC.

November 8, 2018 EX-99.1

Trupanion Reports Third Quarter 2018 Results

Exhibit 99.1 Trupanion Reports Third Quarter 2018 Results SEATTLE, WA. November 8, 2018 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the third quarter ended September 30, 2018. “Performance in the third quarter was particularly strong, led by continued success in growing same store sales, improving conversion rat

November 1, 2018 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 1, 2018 TRUPANION, INC.

November 1, 2018 EX-99.1

Trupanion Issues Statement Regarding Conclusion of Points Program

Exhibit 99.1 Trupanion Issues Statement Regarding Conclusion of Points Program SEATTLE, November 1, 2018 - Trupanion, Inc. (Nasdaq: TRUP) a leader in medical insurance for cats and dogs, today issued the following statement: At Trupanion we are constantly testing ways we can surprise and delight the teams that work in support of the best care for pets. In response to market speculation and misinfo

October 30, 2018 EX-99.1

October 30, 2018

Exhibit 99.1 October 30, 2018 Trupanion Provides Public Statement on Business Practices In our ongoing efforts to be transparent, we are providing an update on the status of our business. Specifically, there has been misinformation in the marketplace about our business practices and the nature of our interactions with regulators. As a result of the misinformation, we felt a clarification was warra

October 30, 2018 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 30, 2018 TRUPANION, INC.

September 7, 2018 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 5, 2018 TRUPANION, INC.

September 7, 2018 EX-99.1

Trupanion Appoints Jackie Davidson, Former CFO of Market Leader, to Board of Directors Announces Changes in Executive Roles

Exhibit 99.1 Trupanion Appoints Jackie Davidson, Former CFO of Market Leader, to Board of Directors Announces Changes in Executive Roles SEATTLE, September 7, 2018 – Trupanion, Inc. (Nasdaq: TRUP) a leader in medical insurance for cats and dogs, announced today the appointment of Jackie Davidson to its Board of Directors, effective September 5, 2018. With over 25 years of experience as an operatin

August 21, 2018 EX-24

EX-24

LIMITED POWER OF ATTORNEY The undersigned hereby constitutes and appoints the responsible officers, attorney and paralegal of Trupanion, Inc.

August 21, 2018 EX-24

EX-24

LIMITED POWER OF ATTORNEY The undersigned hereby constitutes and appoints the responsible officers, attorney and paralegal of Trupanion, Inc.

August 13, 2018 8-K

Entry into a Material Definitive Agreement, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 9, 2018 TRUPANION, INC.

August 9, 2018 S-3ASR

TRUP / Trupanion, Inc. S-3ASR

As filed with the Securities and Exchange Commission on August 9, 2018 Registration No.

August 3, 2018 EX-10.1

Third Amendment to Senior Credit Facility Loan and Security Agreement, dated June 28, 2018, between Pacific Western Bank, Western Alliance Bank and the Registrant.

Exhibit 10.1 THIRD AMENDMENT TO LOAN AND SECURITY AGREEMENT THIS THIRD AMENDMENT TO LOAN AND SECURITY AGREEMENT (this “Amendment”), is entered into as of June 28, 2018, by and among TRUPANION, INC., a Delaware corporation (“Trupanion”), TRUPANION MANAGERS USA, INC., an Arizona corporation (“Trupanion Managers”; together with Trupanion, individually and collectively, “Borrower”), the several banks

August 3, 2018 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-36537 TRUPANION,

August 3, 2018 EX-10.2

Third Amendment to Lease Agreement, dated May 9, 2018 between Benaroya Capital Company, LLC and Trupanion, Inc.

Exhibit 10.2 THIRD LEASE AMENDMENT Between BENAROYA CAPITAL COMPANY, LLC and TRUPANION, INC. This Third Lease Amendment dated May 9, 2018 is attached to and made part of that certain Lease dated August 10, 2015 as amended by a First Lease Amendment dated April 29, 2016 and as further amended by a Second Lease Amendment dated October 20, 2017 (collectively the “Lease”) between Benaroya Capital Comp

August 2, 2018 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 2, 2018 TRUPANION, INC.

August 2, 2018 EX-99.1

Trupanion Reports Second Quarter 2018 Results

Exhibit 99.1 Trupanion Reports Second Quarter 2018 Results SEATTLE, WA. August 2, 2018 - Trupanion, Inc. (Nasdaq: TRUP), a leading provider of medical insurance for cats and dogs, today announced financial results for the second quarter ended June 30, 2018. “Overall, Q2 was a productive quarter of consistent growth that culminated with a successful equity financing. This financing positions us to

June 29, 2018 8-K

Entry into a Material Definitive Agreement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 28, 2018 TRUPANION, INC. (Exact name of registrant as specified in its charter) Delaware 001-36537 83-0480694 (State or other jurisdiction of incorporation) (Commission File Numb

June 22, 2018 EX-1.1

1,818,182 Shares TRUPANION, INC. Common Stock UNDERWRITING AGREEMENT

Exhibit 1.1 Execution Version 1,818,182 Shares TRUPANION, INC. Common Stock UNDERWRITING AGREEMENT June 21, 2018 STIFEL, NICOLAUS & COMPANY, INCORPORATED As representative of the several Underwriters named in Schedule I hereto c/o Stifel, Nicolaus & Company, Incorporated One Montgomery Street, Suite 3700 San Francisco, CA 94104 Ladies and Gentlemen: Trupanion, Inc., a Delaware corporation (the “Co

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