TRUP Form 144: Notice of Proposed Sale of 3,603 Shares

TRUP discloses a Form 144 notice reporting proposed and recent sales of Common stock.

Rhea-AI Filing Summary

TRUP discloses a Form 144 notice reporting proposed and recent sales of Common stock. The filing lists 3,603 shares of restricted Common stock as the securities to be sold and shows recent dispositions by John Gallagher: 431 shares on 04/28/2026 for $11,839.57 and 430 shares on 03/30/2026 for $10,952.10. The broker/filing agent is noted as Morgan Stanley Smith Barney LLC.

Insights

Corporate Governance Analyst

Form 144 lists proposed resale of restricted common stock and recent small dispositions by an affiliate.

The filing identifies 3,603 shares of restricted Common stock as the securities to be sold and records two recent sales by John Gallagher of 431 and 430 shares on 04/28/2026 and 03/30/2026 respectively, with the dollar amounts shown in the excerpt.

These quantities are modest; cash‑flow treatment and any transfer restrictions beyond the label "Restricted Stock" are not stated in the excerpt. Subsequent SEC filings or broker confirmations would show whether further resale activity follows the notice.

Key Figures

Restricted shares listed: 3,603 shares Sale on 04/28/2026: 431 shares Sale on 03/30/2026: 430 shares

3 metrics

Restricted shares listed 3,603 shares Securities To Be Sold (Restricted Stock) dated 08/25/2023

Sale on 04/28/2026 431 shares Disposition by John Gallagher on <date>04/28/2026</date> for <money>$11,839.57</money>

Sale on 03/30/2026 430 shares Disposition by John Gallagher on <date>03/30/2026</date> for <money>$10,952.10</money>

Key Terms

Restricted Stock, Form 144, Issuer

3 terms

Restricted Stock financial

"Securities To Be Sold | Common | 08/25/2023 | 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.

Form 144 regulatory

"Content metadata indicates form_type: 144"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Issuer regulatory

"Securities To Be Sold ... ISSUER"

FAQ

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

What does TRUP's Form 144 report?

The filing reports a proposed resale of Common stock and recent sales by an affiliate. It lists 3,603 restricted shares and two recent dispositions of 431 and 430 shares with their proceeds shown.

Who sold shares according to the TRUP excerpt?

The excerpt names John Gallagher as the seller of recent shares. It records sales of 431 shares on 04/28/2026 and 430 shares on 03/30/2026 with the dollar amounts shown.

How many restricted shares does the Form 144 list for TRUP?

The filing lists 3,603 shares of restricted Common stock as the securities to be sold. The entry is labeled "Restricted Stock" with an associated date of 08/25/2023 in the excerpt.

Does the excerpt state who is the broker handling the sale?

Yes. The broker/filer is shown as Morgan Stanley Smith Barney LLC, Executive Financial Services with an address at 1 New York Plaza, 8th Floor, New York, NY.

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

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Accepted by SEC EDGAR 05/28/2026 - 04:05 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	3603	78153.39	43620472	05/28/2026	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	08/25/2023	Restricted Stock	ISSUER			3603	08/25/2023	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	04/28/2026	431	11839.57
JOHN GALLAGHER 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	03/30/2026	430	10952.10

144: Remarks and Signature

Remarks	The securities to be sold were acquired upon the vesting of restricted stock during the period of 08/25/2023 through 05/22/2026.
Date of Notice	05/28/2026
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)