In back in 2011, Victoria Barret told the story of how Dropbox’s Drew Houston turned down an offer from Apple — from Steve Jobs himself! — to buy Dropbox for a nine-figure sum. Dropbox’s fortunes have far from waned, with the service now boasting over 100 million users and an estimated valuation of $4 billion, but we’ve heard rumblings that Apple may once again be looking to acquire Dropbox in an effort to provide a true distributed filesystem for iOS.
According to a source within the company, Apple CEO Tim Cook is a huge Dropbox fan, requiring all corporate documents to appear in his Dropbox folder so he can access them quickly on any of his devices, wherever he may be. Plus, he is reportedly unhappy about how difficult it is to move documents back and forth between his iPad and Mac, and to share documents with colleagues. Our source says Cook has expressed his frustrations in meetings, echoing about the Maps situation and saying, “we screwed up” with regard to documents in iOS.
Since its inception, iOS has suffered from clumsy, app-based file handling. Sandboxing apps away from each other increases security but forces users to jump through hoops to copy files between apps and devices, wastes limited device space on duplicated data, and makes it all the harder to collaborate with others. Many developers have sidestepped iOS’s limitations in this respect by integrating support for Dropbox, thus enabling their apps to read and write documents stored on the cloud file-sharing service. Dropbox support also lets anyone with whom a document is shared work with whatever application and platform is appropriate, rather than being limited to Apple’s platforms and iCloud-savvy apps, Mac versions of which can be distributed only through the Mac App Store.
Although Dropbox has only become more popular since Apple’s last attempt to buy the company, Apple’s need for such a solution has become greater, with customers expressing exasperation at iOS file handling and competitors spinning up Dropbox-like services, most notably Google Drive and Microsoft’s SkyDrive (see “,” 24 April 2012). The price of acquiring Dropbox would undoubtedly be steep — some have suggested that Apple might have to pony up as much as $10 billion. But as our source related, Tim Cook is unperturbed by this, commenting, “It’s not like Apple doesn’t have the money, and what’s it good for if not to buy the things I want?”
One current concern — surrounding  — would not be addressed were Apple to buy Dropbox, since Dropbox’s technology is still entirely document-based. It’s entirely possible that Dropbox is working on extending the Dropbox API to support database-level syncing as well, but the company has made no public statements to that effect.
The real question, if Tim Cook were to be successful in convincing Dropbox’s executive team to sell out, is what would happen to Dropbox users on non-Apple platforms? Apple has never been enthusiastic about Windows programs, and it’s difficult to see Apple bothering to maintain an Android or Windows Mobile client. Such a move would undoubtedly be a boon for Dropbox competitors like SugarSync and Dolly Drive, though neither has the same level of API-based integration with independent apps.