2/24/2018 S-1 Table of Contents CAPITALIZATION The following table sets forth cash and cash equivalents, as well as our capitalization, as of December 31, 2017, as follows: • on an actual basis; • on a pro forma basis, giving effect to (i) the Capital Stock Conversions, as if such conversions had occurred on December 31, 2017, (ii) the filing and effectiveness of our amended and restated certificate of incorporation in Delaware that will become effective immediately prior to the completion of this offering, (iii) stock­based compensation expense of $415.6 million associated with the RSU Settlement, (iv) the net issuance of 23,844,147 shares of our Class B common stock upon the RSU Settlement, (v) the borrowing of $ under our revolving credit facility to satisfy our tax withholding and remittance obligations related to the RSU Settlement, and (vi) a cash payment of $ to satisfy our tax withholding and remittance obligations related to the RSU Settlement, which amounts in (v) and (vi) are based upon the assumed initial public offering price of $ per share, which is the midpoint of the estimated offering price range set forth on the cover page of this prospectus; and • on a pro forma as adjusted basis, giving effect to (i) the pro forma adjustments set forth above, (ii) the sale and issuance by us of shares of our Class A common stock in this offering, based upon the assumed initial public offering price of $ per share, which is the midpoint of the estimated offering price range set forth on the cover page of this prospectus, and after deducting estimated underwriting discounts and commissions and estimated offering expenses payable by us, (iii) the conversion of shares of our Class B common stock held by certain selling stockholders into an equivalent number of shares of our Class A common stock upon the sale by the selling stockholders in this offering, and (iv) the use of proceeds from the offering to repay $ drawn down under our revolving credit facility to satisfy our tax withholding and remittance obligations related to the RSU Settlement. 48 https://www.sec.gov/Archives/edgar/data/1467623/000119312518055809/d451946ds1.htm 55/235

Dropbox S-1 | Interactive Prospectus - Page 55 Dropbox S-1 | Interactive Prospectus Page 54 Page 56