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Dropbox, Inc. Chief Financial Officer Ross Tennenbaum reported a tax-related share disposition tied to restricted stock units. On May 15, 2026, 20,325 shares of Class A common stock were withheld by Dropbox at $26.20 per share to satisfy tax withholding and remittance obligations upon RSU vesting. This was an automatic tax-withholding event, not an open‑market sale. After this transaction, Tennenbaum directly held 779,605 shares of Class A common stock. Some of his holdings include restricted stock units that are scheduled to vest under an applicable schedule through November 15, 2029, and any unvested units will be cancelled if he ceases to be a service provider.
DROPBOX, INC. executive Ashraf Alkarmi, General Manager, Core, reported a routine tax-related share disposition. On May 15, 2026, 21,446 shares of Class A Common Stock were withheld by Dropbox at $26.20 per share to cover tax withholding and remittance obligations tied to vesting restricted stock units (RSUs).
Following this net settlement, Alkarmi directly holds 624,895 shares of Class A Common Stock. Certain holdings are RSUs, each representing the right to receive one Class A share under a vesting schedule running through November 15, 2029; any unvested RSUs are cancelled if his service ends.
Dropbox, Inc. Chief Legal Officer William T. Yoon reported recent share activity in Class A common stock. On May 18, 2026, he completed open-market sales totaling 7,230 shares at prices of $27.80 and $27.2826 per share under a Rule 10b5-1 trading plan.
Earlier, on May 15, 2026, 16,124 shares were withheld by Dropbox to satisfy tax obligations tied to the vesting and net settlement of previously reported restricted stock units. After these transactions, he directly holds 366,963 shares of Class A common stock, and certain holdings remain in restricted stock units vesting through February 15, 2030.
Dropbox Chief Technology Officer Ali Dasdan reported recent stock transactions in Dropbox Class A Common Stock. On May 18, 2026, he sold a total of 5,666 shares in open-market trades at weighted average prices around the high-$27 range under a Rule 10b5-1 trading plan. On May 15, 2026, 19,254 shares were withheld by Dropbox to cover tax obligations tied to vesting restricted stock units, which is not an open-market sale. Following these transactions, he directly holds 514,611 shares of Dropbox Class A Common Stock.
Dropbox, Inc. Chief Accounting Officer Sarah Elizabeth Schubach reported two movements in Class A Common Stock. On May 19, 2026, she completed an open-market sale of 1,306 shares at $28.14 per share, leaving her with 131,120 shares held directly. Earlier, on May 15, 2026, 3,680 shares were withheld at $26.20 per share to cover tax obligations tied to vesting restricted stock units. The sale was executed under a Rule 10b5-1 trading plan adopted on May 16, 2025.
Company affiliate submitted a Form 144 notice to sell Common Stock (DBX) tied to Restricted Stock Units. The filing lists multiple 10b5-1 sales executed in March–April 2026 with individual lots of 1,415, 1,416, and 1,769 shares and cash amounts shown alongside each lot. The securities to be sold are described as Restricted Stock Units with an effective date of 05/15/2026.
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.
Ali Dasdan proposes sale of Common stock under Rule 144. The notice lists 5,666 shares of Common stock tied to Restricted Stock Units dated 05/15/2026 and names Morgan Stanley Smith Barney LLC as the broker. The excerpt also shows a 10b5-1 sale of 7,306 shares on 02/26/2026 for $181,855.84.
DBX affiliate files a proposed sale of 7,230 shares of Common Stock consisting of restricted stock units dated 05/15/2026. The filing also reports prior 10b5-1 sales of 9,175 shares on 03/11/2026 for $237,897.35.