Trupanion insider plans sale of 430 common shares

Trupanion insider John Gallagher has filed a Form 144 notice to sell 430 shares of Trupanion common stock.

Rhea-AI Filing Summary

Trupanion insider John Gallagher has filed a Form 144 notice to sell 430 shares of Trupanion common stock. The planned sale, through Morgan Stanley Smith Barney LLC on NASDAQ, has an aggregate market value of 13618.10 and is targeted for 01/28/2026.

The shares to be sold come from multiple restricted stock awards acquired from the issuer between 02/25/2022 and 02/25/2023, in blocks ranging from 7 to 132 shares. Trupanion had 43,198,164 common shares outstanding at the time listed.

Over the past three months, Gallagher has already sold Trupanion common stock, including 6,383 shares on 11/28/2025 for gross proceeds of 222282.86 and 430 shares on 12/29/2025 for 16146.50.

FAQ

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

What does the Form 144 filing for TRUP by John Gallagher disclose?

The filing discloses that John Gallagher plans to sell 430 Trupanion common shares through Morgan Stanley Smith Barney LLC on NASDAQ, with an aggregate market value of 13618.10. It also outlines prior sales and the restricted stock origins of these shares.

How many Trupanion (TRUP) shares is John Gallagher planning to sell?

John Gallagher plans to sell 430 shares of Trupanion common stock. The planned transaction, listed under Rule 144, is to be executed on NASDAQ through Morgan Stanley Smith Barney LLC, with the filing showing an aggregate market value of 13618.10 for this block.

What prior Trupanion (TRUP) stock sales by John Gallagher are reported?

The notice reports that Gallagher sold 6,383 Trupanion common shares on 11/28/2025 for gross proceeds of 222282.86, and 430 shares on 12/29/2025 for 16146.50. These transactions occurred within the three months preceding the new planned sale.

How were the Trupanion (TRUP) shares being sold under Form 144 originally acquired?

The shares were acquired as restricted stock directly from the issuer. The filing lists several grant dates between 02/25/2022 and 02/25/2023, with individual acquisitions ranging from 7 to 132 shares, all marked as not involving special non-cash payment terms.

What is the outstanding share count of Trupanion (TRUP) referenced in the Form 144?

The document states that 43,198,164 Trupanion common shares were outstanding. This figure provides context for the relative size of the 430-share planned sale and the earlier reported transactions but is not itself part of the sale notice amount.

Which broker and exchange are involved in the planned TRUP share sale?

The filing shows that Morgan Stanley Smith Barney LLC Executive Financial Services is the broker handling the sale, with trades expected on the NASDAQ exchange. The approximate sale date listed for the 430 shares is 01/28/2026.

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

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Accepted by SEC EDGAR 01/28/2026 - 04:00 PM 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	0001967117
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	JOHN GALLAGHER
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

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	430	13618.10	43198164	01/28/2026	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	02/28/2022	Restricted Stock	ISSUER			22	02/28/2022	Not Applicable
Common	02/25/2023	Restricted Stock	ISSUER			7	02/25/2023	Not Applicable
Common	11/25/2022	Restricted Stock	ISSUER			109	11/25/2022	Not Applicable
Common	02/25/2022	Restricted Stock	ISSUER			132	02/25/2022	Not Applicable
Common	08/25/2022	Restricted Stock	ISSUER			115	08/25/2022	Not Applicable
Common	05/25/2022	Restricted Stock	ISSUER			45	05/25/2022	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
JOHN GALLAGHER 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	12/29/2025	430	16146.50
JOHN GALLAGHER 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	11/28/2025	6383	222282.86

144: Remarks and Signature

Remarks
Date of Notice	01/28/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	08/20/2025
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/ John Ross Gallagher
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)