[144] Dropbox, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 notice for Dropbox, Inc. (DBX): An insider sale is disclosed for 2,500 shares of common stock executed through Morgan Stanley Smith Barney LLC with an aggregate market value of $72,312.50. The shares are scheduled for sale on 08/29/2025 on NASDAQ. The securities were originally granted as restricted stock units (RSUs) and acquired on 02/15/2025 from the issuer; payment information is listed as N/A. The filing also lists multiple prior sales under a Rule 10b5-1 trading plan by Timothy Regan between 05/30/2025 and 08/15/2025 totaling 25,000 shares sold in separate transactions with gross proceeds shown per trade. The filing is marked as a LIVE submission.

Positive

• Disclosure includes full transactional details (broker, sale date, shares, market value, exchange).
• Securities originated as RSUs with acquisition date specified, clarifying the nature of the holdings.
• Use of a Rule 10b5-1 sales plan for multiple prior sales indicates pre-arranged transactions and procedural compliance.

Negative

• None.

Insights

Securities Analyst

TL;DR: Routine insider sale of recently vested RSUs executed under a 10b5-1 plan; transaction size is immaterial to total shares outstanding.

The filing reports a proposed sale of 2,500 common shares with market value $72,312.50 scheduled for 08/29/2025, acquired as RSUs on 02/15/2025. Multiple prior 10b5-1 plan sales by Timothy Regan are disclosed, indicating ongoing plan-driven dispositions rather than ad hoc sales. Given the issuer's reported outstanding shares of 193,414,444, the individual transactions disclosed are de minimis relative to the float and unlikely to be material to valuation.

Corporate Governance Expert

TL;DR: Disclosure aligns with Rule 144 and 10b5-1 transparency expectations; no red flags in the filing itself.

The notice identifies the broker, sale date, acquisition date and nature (RSUs), and enumerates recent 10b5-1 plan sales with gross proceeds, satisfying routine disclosure norms. The signer represents absence of undisclosed material nonpublic information as required. There is no indication of unusual trading timing or exceptions in the form; materiality would depend on broader context not provided in this filing.

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	2500	72312.50	193414444	08/29/2025	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	02/15/2025	Restricted Stock Units	Issuer			2500	02/15/2025	N/A

* 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
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	08/15/2025	2500	69879.50
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	07/29/2025	2500	69944.25
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	07/15/2025	2500	67070.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	07/01/2025	10000	279392.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	06/30/2025	2500	71000.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	06/13/2025	2500	70245.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	05/30/2025	2500	71950.00

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 does Dropbox's (DBX) Form 144 disclose?

The notice discloses a proposed sale of 2,500 common shares with an aggregate market value of $72,312.50, scheduled for 08/29/2025, to be executed on NASDAQ.

Who acquired the securities and how were they obtained?

The 2,500 shares were acquired as restricted stock units (RSUs) on 02/15/2025, with the issuer listed as the source.

Which broker is handling the sale in the Form 144?

The sale is listed with Morgan Stanley Smith Barney LLC, Executive Financial Services, 1 New York Plaza, New York, NY as the broker.

Are there prior sales by the same person reported?

Yes. The filing lists multiple prior 10b5-1 plan sales by Timothy Regan from 05/30/2025 through 08/15/2025, totaling 25,000 shares across several transactions with provided gross proceeds per trade.

How large is this transaction relative to outstanding shares?

The filing reports 193,414,444 shares outstanding; the proposed 2,500-share sale is immaterial relative to that total as stated in the filing.