Trupanion holder plans $25K stock sale

Security holder Margaret R. Tooth filed a Rule 144 notice to resell 1,000 Trupanion common shares previously received as restricted stock.

Rhea-AI Filing Summary

TRUPANION, INC. (TRUP) is the issuer for a planned resale of shares by security holder Margaret R. Tooth under Rule 144. The notice covers 1,000 shares of common stock, with an indicated aggregate market value of $25,000.00, to be sold through Morgan Stanley Smith Barney LLC on NASDAQ around September 11, 2026.

The shares were acquired as restricted stock from the issuer on February 25, 2022, and the filing also notes a prior sale of 978 shares during the past three months for proceeds of $28,410.90.

Key Figures

Shares to be sold: 1,000 shares Aggregate market value of planned sale: $25,000.00 Approximate sale date: September 11, 2026 +3 more

6 metrics

Shares to be sold 1,000 shares Planned sale of Trupanion common stock under Rule 144

Aggregate market value of planned sale $25,000.00 Indicated value for the 1,000 TRUP shares to be sold

Approximate sale date September 11, 2026 Approximate date of sale for the 1,000 TRUP shares

Past 3 months shares sold 978 shares Shares of Trupanion common stock sold on August 11, 2026

Proceeds from past 3 months sale $28,410.90 Total proceeds from sale of 978 TRUP shares on August 11, 2026

Acquisition date of restricted stock February 25, 2022 Date the 1,000 restricted TRUP shares were acquired from the issuer

Key Terms

Rule 144, restricted stock, aggregate market value

3 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

restricted stock financial

"Common | 02/25/2022 | Restricted Stock | ISSUER"

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

"Common | Morgan Stanley Smith Barney LLC ... | 1000 | 25000.00"

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.

What does the Form 144 filing disclose for TRUP?

It discloses that Margaret R. Tooth plans to sell 1,000 shares of TRUPANION, INC. common stock under Rule 144, with an indicated aggregate market value of $25,000.00, through Morgan Stanley Smith Barney LLC on NASDAQ around September 11, 2026.

How many TRUP shares is the filer planning to sell under this Form 144?

The filer, Margaret R. Tooth, plans to sell 1,000 shares of Trupanion common stock under this Rule 144 notice, with an indicated aggregate market value of $25,000.00 at the time of the notice.

When were the TRUP shares in this Form 144 acquired and in what form?

The 1,000 TRUP shares covered by this notice were acquired on February 25, 2022 as restricted stock from TRUPANION, INC. The filing describes the nature of acquisition as “Restricted Stock” and the source as “Issuer.”

Which broker will handle the planned sale of TRUP shares?

The planned sale of the 1,000 TRUP shares will be handled by Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004, with the shares to be sold on NASDAQ.

Have there been recent TRUP share sales by the same person before this Form 144?

Yes. The filing reports that 978 shares of Trupanion common stock were sold by Margaret R. Tooth on August 11, 2026, for total proceeds of $28,410.90 during the past three months prior to this notice.

What is the approximate date of sale for the TRUP shares in this Form 144?

The approximate date of sale for the 1,000 TRUP shares covered by this Rule 144 notice is listed as September 11, 2026, with the shares expected to be sold on NASDAQ through Morgan Stanley Smith Barney LLC.

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

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Available on EDGAR 09/11/2026 - 04:09 PM EDT Accepted by SEC EDGAR 09/11/2026 - 04:08 PM EDT Learn about SEC filing dates

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 R 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	1000	25000.00	43872611	09/11/2026	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			1000	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	08/11/2026	978	28410.90

144: Remarks and Signature

Remarks
Date of Notice	09/11/2026
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)