Trupanion officer plans $107K stock sale

Rhea-AI Filing Summary

TRUPANION, INC. (TRUP) had a notice filed under Rule 144 by officer John Ross Gallagher for a planned sale of its common stock. The notice covers 3,604 shares of common stock, held at Morgan Stanley Smith Barney LLC Executive Financial Services, with an aggregate market value of $107,038.80 and reference to 43,872,611 shares outstanding as context. The securities to be sold were acquired upon the vesting of restricted stock during the period from 11/25/2023 through 08/22/2026. Gallagher also reports prior sales over the past three months of 431 shares on each of 06/29/2026 and 07/28/2026, for proceeds of $10,925.85 and $10,809.48, respectively.

Key Figures

Shares to be sold: 3,604 shares of common stock Aggregate market value of planned sale: $107,038.80 Shares outstanding: 43,872,611 shares +4 more

7 metrics

Shares to be sold 3,604 shares of common stock Planned sale under Rule 144 for John Ross Gallagher

Aggregate market value of planned sale $107,038.80 Value associated with 3,604 shares to be sold

Shares outstanding 43,872,611 shares Referenced share count for TRUPANION, INC. common stock

Shares sold on 07/28/2026 431 shares Common stock sales during the past 3 months

Proceeds on 07/28/2026 sale $10,809.48 Sale of 431 shares of common stock

Shares sold on 06/29/2026 431 shares Common stock sales during the past 3 months

Proceeds on 06/29/2026 sale $10,925.85 Sale of 431 shares of common stock

Key Terms

Rule 144, restricted stock, Securities To Be Sold, Securities Sold During The Past 3 Months

4 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

"The securities to be sold were acquired upon the vesting of 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.

Securities To Be Sold financial

"144: Securities To Be Sold Common | 11/25/2023 | Restricted Stock"

Securities Sold During The Past 3 Months financial

"144: Securities Sold During The Past 3 Months JOHN GALLAGHER"

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 officer John Ross Gallagher filed a Rule 144 notice to sell 3,604 shares of TRUPANION, INC. common stock, with an aggregate market value of $107,038.80, acquired through vesting of restricted stock between 11/25/2023 and 08/22/2026.

How many TRUP shares is John Gallagher planning to sell under this Form 144?

John Gallagher indicates an intention to sell 3,604 shares of TRUPANION, INC. common stock under Rule 144, related to restricted stock that vested between 11/25/2023 and 08/22/2026.

What is the aggregate market value of the TRUP shares covered by this Form 144?

The Form 144 lists an aggregate market value of $107,038.80 for the 3,604 shares of TRUPANION, INC. common stock referenced in the planned Rule 144 sale.

What TRUP shares has John Gallagher sold in the past three months?

Over the past three months, John Gallagher reports sales of 431 shares of TRUP common stock on 06/29/2026 for $10,925.85 and 431 shares on 07/28/2026 for $10,809.48.

How many TRUP shares were outstanding as referenced in the Form 144?

The Form 144 references 43,872,611 shares of TRUPANION, INC. common stock as an outstanding-share figure, providing context for the planned Rule 144 sale.

How were the TRUP shares to be sold by John Gallagher acquired?

The shares to be sold were acquired upon the vesting of restricted stock during the period from 11/25/2023 through 08/22/2026, as stated in the remarks section of the Form 144.

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

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Available on EDGAR 08/28/2026 - 04:41 PM EDT Accepted by SEC EDGAR 08/28/2026 - 04:41 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	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	3604	107038.80	43872611	08/28/2026	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	11/25/2023	Restricted Stock	ISSUER			3604	11/25/2023	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	07/28/2026	431	10809.48
JOHN GALLAGHER 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	06/29/2026	431	10925.85

144: Remarks and Signature

Remarks	The securities to be sold were acquired upon the vesting of restricted stock during the period of 11/25/2023 through 8/22/2026.
Date of Notice	08/28/2026
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)