TRUP Form 144/A — 30,369 Shares Proposed Sale; Recent 19,631-Share Sale

Rhea-AI Filing Summary

Trupanion insider sale notice: This Form 144/A reports a proposed sale of 30,369 shares of Trupanion common stock via Fidelity Brokerage Services (245 Summer Street, Boston, MA) with an aggregate market value of $1,357,943.00. The shares are listed as to be sold approximately on 09/04/2025 on NASDAQ. The filing lists the acquisition history for these shares showing multiple stock awards and one stock option from Trupanion dated between 2018 and 2025, with amounts for each award. The filing also discloses a sale during the past three months: Darryl Rawlings (c/o Trupanion) sold 19,631 shares on 09/03/2025 for gross proceeds of $878,487.25. The filer certifies no undisclosed material adverse information.

Positive

• None.

Negative

• Proposed insider sale of 30,369 Trupanion common shares reported in Form 144/A
• Recent executed sale: Darryl Rawlings sold 19,631 shares on 09/03/2025 for $878,487.25
• Concentration of shares originates from multiple compensation stock awards and one option issued by Trupanion between 2018 and 2025

Insights

Securities Analyst

TL;DR: Routine insider notice of proposed stock sale; lists award history and a recent executed sale.

The Form 144/A documents a proposed disposition of 30,369 Trupanion common shares through a broker on NASDAQ with an indicated aggregate market value of $1,357,943.00 and includes a detailed acquisition schedule showing multiple compensation-related stock awards and one stock option granted by the company from 2018 through 2025. The filing additionally reports a sale executed on 09/03/2025 by Darryl Rawlings of 19,631 shares for $878,487.25. This notice is procedural under Rule 144 and supplies transparency about timing and provenance of the shares; it does not provide operational or earnings data.

Corporate Governance Expert

TL;DR: Insider compliance disclosure; provides provenance of shares and confirms no undisclosed material information.

The submission appears to be a compliance filing to satisfy Rule 144 prerequisites for an insider sale, enumerating the grant dates and quantities for the securities to be sold and affirming the signer is not aware of undisclosed material adverse information. The record of a recent sale (9/3/2025) is included, which helps stakeholders track insider liquidity events. The form contains no discussion of executive role changes, trading plans, or other governance actions.

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/A

144/A: Filer Information

Filer CIK
Filer CCC
Previous Accession Number Of The Filing
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144/A: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

144/A: 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	Fidelity Brokerage Services LLC 245 Summer Street Boston MA 02110	30369	1357943.00	4299467	09/04/2025	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/A: 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	11/25/2021	Stock award	Trupanion			2925	11/25/2021	Compensation
Common	02/22/2021	Stock award	Trupanion			54	02/22/2021	Compensation
Common	11/25/2020	Stock award	Trupanion			2062	11/25/2020	Compensation
Common	02/25/2021	Stock award	Trupanion			6743	02/25/2021	Compensation
Common	08/25/2021	Stock award	Trupanion			2926	08/25/2021	Compensation
Common	02/25/2022	Stock award	Trupanion			11037	02/25/2022	Compensation
Common	05/25/2021	Stock award	Trupanion			2925	05/25/2021	Compensation
Common	08/25/2022	Stock award	Trupanion			3847	08/25/2022	Compensation
Common	05/25/2022	Stock award	Trupanion			3846	05/25/2022	Compensation
Common	08/25/2020	Stock award	Trupanion			2062	08/25/2020	Compensation
Common	02/25/2023	Stock award	Trupanion			7560	02/25/2023	Compensation
Common	11/25/2024	Stock award	Trupanion			6308	11/25/2024	Compensation
Common	11/25/2022	Stock award	Trupanion			3846	11/25/2022	Compensation
Common	02/25/2021	Stock option	Trupanion			439	02/25/2021	cash/check
Common	08/25/2024	Stock award	Trupanion			7517	08/25/2024	Compensation
Common	11/25/2019	Stock award	Trupanion			740	11/25/2019	Compensation
Common	11/25/2020	Stock award	Trupanion			2062	11/25/2020	Compensation
Common	02/25/2020	Stock award	Trupanion			5382	02/25/2020	Compensation
Common	02/25/2025	Stock award	Trupanion			3684	02/25/2025	Compensation
Common	05/25/2019	Stock award	Trupanion			740	05/25/2019	Compensation
Common	08/25/2023	Stock award	Trupanion			4376	08/25/2023	Compensation
Common	02/25/2019	Stock	Trupanion			2959	02/25/2019	Compensation
Common	02/22/2025	Stock award	Trupanion			7500	02/22/2025	Compensation
Common	11/25/2023	Stock award	Trupanion			4259	11/25/2023	Compensation
Common	11/19/2018	Stock award	Trupanion			100477	11/19/2018	Compensation
Common	11/12/2018	Stock award	Trupanion			100477	11/12/2018	Compensation
Common	08/25/2019	Stock award	Trupanion			740	08/25/2019	Compensation

* 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/A: 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
Darryl Rawlings c/o Trupanion 6100 4th avenue South STE 400 Seattle WA 98108	Common Stock	09/03/2025	19631	878487.25

144/A: Remarks and Signature

Remarks

Date of Notice

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does the Form 144/A for TRUP disclose?

The filing reports a proposed sale of 30,369 Trupanion common shares with aggregate market value of $1,357,943.00, to be sold on 09/04/2025 on NASDAQ.

Who executed a recent sale disclosed in this filing?

Darryl Rawlings (c/o Trupanion) sold 19,631 shares on 09/03/2025 for gross proceeds of $878,487.25.

Where will the proposed shares be sold and through which broker?

The proposed sale is listed through Fidelity Brokerage Services LLC, 245 Summer Street, Boston, MA, and the securities exchange is NASDAQ.

What is the origin of the shares listed for sale?

The acquisition table shows the shares were acquired primarily as stock awards from Trupanion between 2018 and 2025, plus one stock option exercised in 2021.

Does the filer assert there is undisclosed material information?

By signing, the person represents they do not know of any material adverse information