[Form 4] Dropbox, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Dropbox insider reporting: Timothy Regan, the companys Chief Financial Officer, reported the net settlement of 26,473 shares of Class A common stock to satisfy tax withholding from vested restricted stock awards/units and the sale of 2,500 shares under a Rule 10b5-1 trading plan at a weighted average price of $27.9518 per share. After these transactions, the filing shows 482,121 shares of Class A common stock beneficially owned by the reporting person. The restricted stock awards and restricted stock units referenced remain subject to vesting schedules through February 15, 2029 and unvested awards will be cancelled if the reporting person ceases to be a service provider.

Positive

• Sale executed under a Rule 10b5-1 plan, which provides pre-established timing and reduces concerns about opportunistic insider trading
• Shares withheld to satisfy tax withholding after vesting, indicating net settlement of restricted awards rather than an additional cash sale
• Significant remaining restricted holdings that vest through February 15, 2029, indicating continued alignment with the company over time

Negative

• Disposition of 2,500 shares reduced the reporting person's beneficial holdings to 482,121 shares
• 26,473 shares were withheld for tax obligations, which reduces immediate share ownership compared with pre-vesting amounts

Insights

Financial Analyst

TL;DR: Routine tax withholding and a small planned sale; not a material change to ownership.

The report documents standard post-vesting activity where 26,473 shares were withheld to satisfy tax obligations from restricted stock awards/units, and a planned sale of 2,500 shares executed under an existing Rule 10b5-1 plan at a weighted average price of $27.9518. The resulting beneficial ownership is 482,121 Class A shares. These actions are procedural and consistent with compensation vesting and a pre-established trading plan rather than ad-hoc disposition.

Corporate Governance Expert

TL;DR: Governance signals are neutral; use of a 10b5-1 plan reduces questions about timing.

The filing discloses the CFOs use of a Rule 10b5-1 plan for the sale, which is a governance best practice for insiders to mitigate questions about trading timing. The report also clarifies that certain shares remain restricted and vest through February 15, 2029, highlighting ongoing equity retention tied to service. No unexpected departures, large unscheduled dispositions, or other governance red flags are present in the disclosed transactions.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

X

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Regan Timothy

(Last) (First) (Middle)

1800 OWENS STREET

SUITE 200

(Street)

SAN FRANCISCO CA 94158

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
DROPBOX, INC. [ DBX ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
08/15/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	08/15/2025		F(1)		26,473	D	$27.73	484,621(2)	D
Class A Common Stock	08/15/2025		S(3)		2,500	D	$27.9518(4)	482,121(2)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. Represents shares that have been withheld by the Issuer to satisfy tax withholding and remittance obligations in connection with the vesting and net settlement of restricted stock units and restricted stock awards previously reported.

2. Certain of these securities are restricted stock awards and restricted stock units. Each restricted stock award or restricted stock unit represents the Reporting Person's right to receive one share of Class A Common Stock, subject to the applicable vesting schedule through February 15, 2029. In the event the Reporting Person ceases to be a Service Provider, the unvested restricted stock awards and restricted stock units will be cancelled by the Issuer.

3. These shares were sold pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 15, 2024.

4. This transaction was executed in multiple trades at prices ranging from $27.78 to $28.09. The price reported above reflects the weighted average sale price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Remarks:

	/s/ Cara Angelmar, Attorney-in-Fact	08/19/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transactions did DBX CFO Timothy Regan report?

The report shows 26,473 Class A shares withheld to satisfy tax withholding from vested restricted awards and a sale of 2,500 shares executed under a Rule 10b5-1 plan at a weighted average price of $27.9518 per share.

How many Class A shares does the reporting person own after the transactions?

The reporting person beneficially owns 482,121 shares of Class A common stock following the reported transactions.

Were the sold shares part of a trading plan?

Yes. The sale of shares was made pursuant to a Rule 10b5-1 trading plan adopted on May 15, 2024, as stated in the filing.

Do any restricted shares remain subject to vesting?

Yes. Certain securities are restricted stock awards and restricted stock units that vest under schedules through February 15, 2029; unvested awards will be cancelled if the reporting person ceases to be a service provider.

What price range were the sold shares executed at?

The sale was executed in multiple trades at prices ranging from $27.78 to $28.09, with the filing reporting a weighted average sale price of $27.9518.