[144] Trupanion, Inc. SEC Filing

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP) Form 144 notifies the proposed sale of 6,451 common shares through Morgan Stanley Smith Barney with an aggregate market value of $291,293.61. The filing lists total shares outstanding of 42,994,675 and an approximate sale date of 09/02/2025 on NASDAQ. The shares to be sold arise from restricted stock awards acquired on 05/22/2025 (3,545 shares) and 08/22/2025 (2,906 shares). The filer also disclosed a prior sale of 2,800 common shares on 08/26/2025 generating $127,573.88 in gross proceeds. The notice includes the standard representation that the seller is not aware of undisclosed material adverse information.

Positive

• Full regulatory disclosure under Rule 144 including broker, quantities, acquisition dates, and prior sales
• Use of a major broker (Morgan Stanley Smith Barney) for the proposed disposition

Negative

• Proposed sale occurs shortly after restricted stock acquisitions (05/22/2025 and 08/22/2025), which may attract investor attention
• Recent prior sale of 2,800 shares on 08/26/2025 indicates ongoing insider selling activity in proximity to this notice

Insights

Financial Analyst

TL;DR: Proposed sale is modest relative to outstanding shares and follows recent restricted stock awards; market impact is likely minimal.

The sale of 6,451 shares equals roughly 0.015% of the reported 42,994,675 shares outstanding, indicating limited potential market impact at the company level. The shares originate from restricted stock grants dated 05/22/2025 and 08/22/2025, which suggests these are routine post-vesting dispositions rather than liquidation of long-held positions. Prior sale of 2,800 shares on 08/26/2025 is disclosed, showing recent insider activity but not at a scale that would materially affect capitalization or liquidity. Overall, data points to routine insider selling activity rather than a material corporate development.

Corporate Governance Expert

TL;DR: Filing meets Rule 144 disclosure requirements; timing of sales relative to acquisition is notable but not inherently indicative of governance issues.

The Form 144 properly names the broker (Morgan Stanley Smith Barney) and details acquisition dates and quantities for the shares to be sold, which is consistent with regulatory compliance for restricted stock dispositions. The seller’s certification that no undisclosed material adverse information exists is included. The proximity between acquisition dates (May and August 2025) and the proposed sale date (September 2025) is factual and should be noted by stakeholders, but by itself does not demonstrate a governance lapse. Documentation appears complete for the purposes of Rule 144 notification.

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
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: 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: 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	6451	291293.61	42994675	09/02/2025	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: 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	05/22/2025	Restricted Stock	ISSUER			3545	05/22/2025	Not Applicable
Common	08/22/2025	Restricted Stock	ISSUER			2906	08/22/2025	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
FAWWAD QURESHI 6100 4th Avenue S, Suite 200 Seattle, WA 98108	Common	08/26/2025	2800	127573.88

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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 shares is the TRUP filer proposing to sell?

The filer proposes to sell 6,451 common shares of Trupanion (TRUP).

When is the proposed sale date listed on the Form 144 for TRUP?

The approximate date of sale is listed as 09/02/2025.

Through which broker will the TRUP shares be sold?

The sale is to be effected through Morgan Stanley Smith Barney LLC.

How many TRUP shares were outstanding according to the filing?

The filing reports 42,994,675 shares outstanding.

Did the filer sell any TRUP shares recently?

Yes, the filer sold 2,800 common shares on 08/26/2025 for gross proceeds of $127,573.88.