[144] DROPBOX, INC. SEC Filing

Rhea-AI Filing Summary

Dropbox, Inc. (DBX) filed a Form 144 reporting a proposed sale of 5,000 shares of common stock through Morgan Stanley Smith Barney, with an aggregate market value of $151,050.00, and an approximate sale date of 10/01/2025 on NASDAQ. The shares were acquired as Restricted Stock Units from the issuer on 02/15/2025.

The filing also discloses multiple recent 10b5-1 plan sales by the same beneficial owner (timed between 07/15/2025 and 09/30/2025) totaling sales shown across six transactions with gross proceeds reported for each sale. The filer certifies, by signature, no undisclosed material adverse information exists as of the plan adoption or instruction date where applicable.

Positive

• Transparent disclosure of the proposed sale amount (5,000 shares) and aggregate market value ($151,050.00).
• Use of 10b5-1 sales plans for prior transactions, with individual trade dates and gross proceeds provided.
• Origin of shares disclosed as Restricted Stock Units acquired from the issuer on 02/15/2025, clarifying basis for sale.

Negative

• Insider selling activity is documented across multiple recent 10b5-1 trades totaling several thousand shares, which increases immediate share supply.
• Filing omits full identity details of the beneficial owner beyond an address for the 10b5-1 plan and does not provide plan adoption dates in the visible remarks, limiting context on timing.

Insights

Securities Analyst

TL;DR: Routine insider sale under Rule 144 and 10b5-1; transparent reporting of RSU-derived shares and recent plan sales.

The Form 144 shows a proposed resale of 5,000 shares acquired as RSUs and lists a series of executed 10b5-1 plan sales over recent months with specific gross proceeds per trade. This is consistent with structured, pre-arranged disposition activity rather than opportunistic market timing. For investors, the filing documents liquidity events by an insider or related person but contains no operational or financial performance information about the company itself. Impact on share supply is limited to the disclosed quantities; materiality depends on overall float, which is not provided in this filing.

Corporate Governance Expert

TL;DR: Proper procedural disclosures for insider sales; reliance on 10b5-1 plans and Rule 144 evident.

The filing includes required declarations and indicates the use of broker-dealer channels and a 10b5-1 plan for prior sales, which supports compliance with insider trading rules. The filer affirms absence of undisclosed material adverse information at the relevant plan-adoption or instruction dates. The document does not include plan adoption dates or the signatory name and lacks context on the identity of the beneficial owner beyond the address shown for the 10b5-1 plan, limiting governance conclusions to procedural compliance rather than motive or timing.

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	5000	151050.00	193414444	10/01/2025	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			5000	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	09/30/2025	1500	46065.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	09/15/2025	1500	46305.00
10b5-1 Sales Plan for TIMOTHY REGAN 1800 Owens Street San Francisco CA 94158	Common	08/29/2025	2500	72525.00
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

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 report?

The Form 144 reports a proposed sale of 5,000 common shares with an aggregate market value of $151,050.00, to be sold through Morgan Stanley Smith Barney on or about 10/01/2025.

How were the 5,000 shares acquired according to the filing?

The shares were acquired as Restricted Stock Units from the issuer on 02/15/2025.

Has the beneficial owner made other recent sales of DBX shares?

Yes. The filing lists six 10b5-1 plan sales between 07/15/2025 and 09/30/2025, with reported gross proceeds for each transaction.

Which broker is handling the proposed sale?

The broker named in the filing is Morgan Stanley Smith Barney LLC Executive Financial Services in New York, NY.

Does the filing state there is undisclosed material information?

By signing, the filer represents they do not know any material adverse information regarding the issuer that has not been publicly disclosed as of the relevant plan adoption or instruction date.