Trupanion's Margaret Tooth proposes $72.9K share sale

Earlier reported sales include 1,000 shares on October 9, 2026, 1,000 on September 11, 2026, and 978 on August 11, 2026.

Available on EDGAR 11/09/2026 - 04:38 PM EST Accepted by SEC EDGAR 11/09/2026 - 04:37 PM EST Learn about SEC filing dates

Rhea-AI Filing Summary

Trupanion, Inc. officer and director Margaret Tooth reported a proposed sale of 2,000 common shares, with an aggregate market value of $72,934.20 and an approximate sale date of November 9, 2026. Morgan Stanley Smith Barney LLC is named as broker. The notice lists May 11, 2026 as the Rule 10b5-1 plan adoption or instruction date.

Key Figures

Proposed sale: 2,000 common shares Aggregate market value: $72,934.20 Common shares sold: 1,000 shares +5 more

8 metrics

Proposed sale 2,000 common shares Approximate sale date November 9, 2026

Aggregate market value $72,934.20 Proposed sale

Common shares sold 1,000 shares October 9, 2026; gross proceeds of $25,840

Gross proceeds $25,840 Sale of 1,000 common shares on October 9, 2026

Common shares sold 1,000 shares September 11, 2026; gross proceeds of $25,000

Gross proceeds $25,000 Sale of 1,000 common shares on September 11, 2026

Common shares sold 978 shares August 11, 2026; gross proceeds of $28,410.90

Gross proceeds $28,410.90 Sale of 978 common shares on August 11, 2026

Key Terms

Rule 10b5-1, Restricted Stock, Aggregate Market Value

3 terms

Rule 10b5-1 regulatory

"Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1"

Rule 10b5-1 is a regulation that allows company insiders to buy or sell their shares at predetermined times, even if they have access to non-public information. It acts like setting a schedule in advance for transactions, helping prevent accusations of unfair trading. This rule provides a way for insiders to plan trades transparently, giving investors confidence that these transactions are not based on hidden information.

Restricted Stock financial

"Nature of Acquisition Transaction: Restricted Stock"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Aggregate Market Value financial

"Number of Shares or Other Units To Be Sold | Aggregate Market Value"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many TRUP shares did Margaret Tooth propose to sell?

Margaret Tooth proposed to sell 2,000 common shares with an aggregate market value of $72,934.20; the approximate sale date is November 9, 2026.

What other TRUP shares did Margaret Tooth sell recently?

Margaret Tooth reported selling 1,000 common shares for gross proceeds of $25,840 on October 9, 2026; 1,000 shares for $25,000 on September 11, 2026; and 978 shares for $28,410.90 on August 11, 2026.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001657025
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	TRUPANION, INC.
SEC File Number	001-36537
Address of Issuer	6100 4th Avenue S, Suite 200 Seattle, WASHINGTON 98108
Phone	(855)-727-9079
Name of Person for Whose Account the Securities are To Be Sold	MARGARET TOOTH
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer
Relationship to Issuer	Director

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	2000	72934.20	43265932	11/09/2026	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	02/25/2022	Restricted Stock	Issuer			2000	02/25/2022	Not Applicable

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
MARGARET R TOOTH 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	10/09/2026	1000	25840.00
MARGARET R TOOTH 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	09/11/2026	1000	25000.00
MARGARET R TOOTH 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	08/11/2026	978	28410.90

144: Remarks and Signature

Remarks
Date of Notice	11/09/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	05/11/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Margaret Rosemary Maria Tooth
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)