Dropbox CEO sells 37,498 shares under 10b5-1 plan

Dropbox CEO Andrew Houston reported an exercise-and-sell transaction involving the company’s dual-class shares.

Rhea-AI Filing Summary

Dropbox CEO Andrew Houston reported an exercise-and-sell transaction involving the company’s dual-class shares. He converted 37,498 shares of Class B Common Stock into the same number of Class A shares at a conversion price of $0.00, then sold 37,498 Class A shares in open-market trades at a weighted average price of $25.9627. The sale was carried out under a Rule 10b5-1 trading plan adopted on March 12, 2025, indicating it was pre-scheduled. After these transactions, he continues to hold substantial positions, including 8,266,666 Class A shares directly and large Class B holdings indirectly through various family trusts that are convertible into Class A on a one-for-one basis with no expiration.

Insider Trade Summary 10b5-1

Exercise and sale activity reported; no spread calculated

Exercise and Sale 8 txns

Insider Houston Andrew

Role Chief Executive Officer

Sold 37,498 shs ($974K)

Approx. gross sale proceeds $974K

Approx. exercise cost $0.00

Type	Security	Shares	Price	Value
Conversion	Class B Common Stock	37,498	$0.00	$0.00
Conversion	Class A Common Stock	37,498	$0.00	$0.00
Sale	Class A Common Stock	37,498	$25.9627	$974K
holding	Class B Common Stock	--	--	--
holding	Class B Common Stock	--	--	--
holding	Class A Common Stock	--	--	--
holding	Class A Common Stock	--	--	--
holding	Class A Common Stock	--	--	--

Holdings After Transaction: Class B Common Stock — 66,859,461 contracts for 500,500 underlying shares (Indirect, See foonote); Class A Common Stock — 1,161,172 shares (Indirect, See Footnote); Class B Common Stock — 7,608,764 contracts (Indirect, See Footnote); Class A Common Stock — 8,266,666 shares (Direct)

Footnotes (9)

1. F1. 37,498 shares of Class B Common Stock were converted into 37,498 shares of Class A Common Stock at the election of the Reporting Person and had no expiration date.
2. F2. Shares held by the Andrew Houston Revocable Trust u/a/d 9/7/2011, for which Reporting Person serves as trustee.
3. F3. These shares were sold pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 12, 2025.
4. F4. This transaction was executed in multiple trades at prices ranging from $25.73 to $26.42. 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.
5. F5. These securities are restricted stock awards of Class A Common Stock. The restricted stock awards vest over a period of up to ten years following the closing of the Issuer's initial public offering of Class A Common Stock, or March 27, 2028, upon achievement of service-based, market-based, and liquidity event-related performance vesting conditions.
6. F6. Shares held by the Houston Remainder Trust u/a/d 12/30/2010, for which Reporting Person serves as trustee.
7. F7. Shares held by The Erin Yu Houston Revocable Trust u/a/d 1/18/2024, for which the Reporting Person's spouse serves as trustee.
8. F8. The Issuer's Class B Common Stock is convertible into the Issuer's Class A Common Stock on a one-for-one basis at the Reporting Person's election and has no expiration date.
9. F9. Shares held by the Houston 2012 Irrevocable Children's Trust u/a/d 4/12/2012, for which Reporting Person serves as trustee.

Key Figures

Shares sold: 37,498 shares Weighted average sale price: $25.9627 per share Shares converted: 37,498 shares +5 more

8 metrics

Shares sold 37,498 shares Class A Common Stock sold in open-market trades on May 14, 2026

Weighted average sale price $25.9627 per share Class A shares sold in multiple trades between $25.73 and $26.42

Shares converted 37,498 shares Class B Common Stock converted into Class A at $0.00 exercise price

Direct Class A holdings 8,266,666 shares Class A Common Stock held directly following transactions

Indirect Class B position 66,358,961 shares Class B Common Stock indirectly held after conversion transaction

Convertible underlying shares 7,608,764 shares Class A shares underlying an indirect Class B position at $0.00 exercise price

10b5-1 plan adoption date March 12, 2025 Date Andrew Houston adopted the trading plan used for this sale

Net buy/sell shares −37,498 shares Net effect of reported buy and sell activity in this Form 4

Key Terms

Rule 10b5-1 trading plan, restricted stock awards, Class B Common Stock, weighted average sale price, +2 more

6 terms

Rule 10b5-1 trading plan regulatory

"These shares were sold pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 12, 2025."

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

restricted stock awards financial

"These securities are restricted stock awards of Class A Common Stock."

Restricted stock awards are company shares given to employees or executives that cannot be sold or transferred until certain conditions — like staying with the company for a set time or meeting performance targets — are met, like a gift that is locked in a safe until rules are satisfied. Investors care because these awards tie management’s pay to company performance, can increase the number of shares outstanding when they become tradable (dilution), and may signal expected future selling pressure or commitment to long-term growth.

Class B Common Stock financial

"37,498 shares of Class B Common Stock were converted into 37,498 shares of Class A Common Stock at the election of the Reporting Person"

A class B common stock is one of multiple types of a company’s ordinary shares that carries specific rights—often different voting power or dividend priority—compared with other classes. For investors it matters because those differences affect how much influence you have over company decisions, the income you might receive, and how freely the shares trade; think of it like owning a car with different keys: some keys let you start the engine and open the trunk, others only unlock the door.

weighted average sale price financial

"The price reported above reflects the weighted average sale price."

performance vesting conditions financial

"upon achievement of service-based, market-based, and liquidity event-related performance vesting conditions."

convertible into the Issuer's Class A Common Stock financial

"The Issuer's Class B Common Stock is convertible into the Issuer's Class A Common Stock on a one-for-one basis"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Dropbox (DBX) CEO Andrew Houston report?

Andrew Houston reported converting 37,498 Class B shares into 37,498 Class A shares, then selling 37,498 Class A shares. The sale was executed as open-market trades under a pre-arranged Rule 10b5-1 trading plan adopted on March 12, 2025.

How many Dropbox (DBX) shares did Andrew Houston sell and at what price?

He sold 37,498 shares of Dropbox Class A Common Stock. The trades were executed at prices ranging from $25.73 to $26.42, with a reported weighted average sale price of approximately $25.9627 per share across the multiple executions.

Were Andrew Houston’s Dropbox (DBX) share sales made under a Rule 10b5-1 plan?

Yes. The filing states the 37,498 Class A shares were sold pursuant to a Rule 10b5-1 trading plan. This plan was adopted by Andrew Houston on March 12, 2025, indicating the sales were pre-scheduled rather than discretionary market-timing trades.

What Dropbox (DBX) shares does Andrew Houston still hold after this Form 4?

After the reported transactions, he holds 8,266,666 shares of Class A Common Stock directly. He also has significant indirect holdings of Class B Common Stock through several family trusts, which are each convertible into Class A shares on a one-for-one basis with no expiration date.

How are Andrew Houston’s Dropbox (DBX) indirect holdings structured?

Indirect holdings are held through multiple trusts, including revocable and irrevocable family trusts where he or his spouse serves as trustee. These trusts collectively own Class A and Class B shares, giving him indirect economic exposure while some voting and administrative powers are exercised in a trustee capacity.

What are the terms of Andrew Houston’s Dropbox (DBX) restricted stock awards?

The filing notes restricted stock awards of Class A Common Stock that vest over up to ten years after Dropbox’s IPO. Vesting continues through March 27, 2028, and depends on service-based, market-based, and liquidity event-related performance vesting conditions specified in the award terms.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/18/2026 - 06:23 PM Learn about SEC filing dates

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^*

Houston Andrew

(Last) (First) (Middle)

1800 OWENS STREET

SUITE 200

(Street)

SAN FRANCISCO CALIFORNIA 94158

(City) (State) (Zip)

UNITED STATES

(Country)

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

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

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/14/2026

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

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

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

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	05/14/2026		C		37,498	A	$0(1)	37,498	I	See Footnote(2)
Class A Common Stock	05/14/2026		S(3)		37,498	D	$25.9627(4)	0	I	See Footnote(2)
Class A Common Stock								8,266,666(5)	D
Class A Common Stock								716,728	I	See Footnote(6)
Class A Common Stock								444,444	I	See Footnote(7)

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
Class B Common Stock	(8)	05/14/2026		C			37,498	(8)	(8)	Class A Common Stock	37,498	$0	66,358,961	I	See foonote(2)
Class B Common Stock	(8)							(8)	(8)	Class A Common Stock	7,608,764		7,608,764	I	See Footnote(6)
Class B Common Stock	(8)							(8)	(8)	Class A Common Stock	500,500		500,500	I	See foonote(9)

Explanation of Responses:

1. 37,498 shares of Class B Common Stock were converted into 37,498 shares of Class A Common Stock at the election of the Reporting Person and had no expiration date.

2. Shares held by the Andrew Houston Revocable Trust u/a/d 9/7/2011, for which Reporting Person serves as trustee.

3. These shares were sold pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 12, 2025.

4. This transaction was executed in multiple trades at prices ranging from $25.73 to $26.42. 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.

5. These securities are restricted stock awards of Class A Common Stock. The restricted stock awards vest over a period of up to ten years following the closing of the Issuer's initial public offering of Class A Common Stock, or March 27, 2028, upon achievement of service-based, market-based, and liquidity event-related performance vesting conditions.

6. Shares held by the Houston Remainder Trust u/a/d 12/30/2010, for which Reporting Person serves as trustee.

7. Shares held by The Erin Yu Houston Revocable Trust u/a/d 1/18/2024, for which the Reporting Person's spouse serves as trustee.

8. The Issuer's Class B Common Stock is convertible into the Issuer's Class A Common Stock on a one-for-one basis at the Reporting Person's election and has no expiration date.

9. Shares held by the Houston 2012 Irrevocable Children's Trust u/a/d 4/12/2012, for which Reporting Person serves as trustee.

Remarks:

	/s/ Cara Angelmar, Attorney-in-Fact	05/18/2026
	** 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.
* Form 4: SEC 1474 (03-26)