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During the Q&A portion of a Macworld/iWorld session last week, an audience member asked: “What not-from-Apple utility do you use the most during a typical workday?” For me, the answer is easy: Dropbox.

Dropbox earns my number one spot because of its versatility and simplicity. If I’m working on an article and want to be certain that the latest version is always on both my Mac Pro and my MacBook, I put the document in Dropbox. If I scan something and my wife wants a copy of it, I drop the file into the Dropbox folder we share. If I use my Mac to get a boarding pass and want it accessible on my iPhone, Dropbox manages that job, too.

  • Answer: Open up your hard drive and navigate to the Users folder. From the Users folder double-click on your username. The Dropbox folder is located in that folder.
  • Tap iTunes & App Store. Tap your Apple ID at the top of the screen, then tap View Apple ID. Tap Subscriptions (about midway through the screen). Tap Cancel Subscription or Cancel Trial. Your account will downgrade to Dropbox Basic (free) at the end of your billing cycle.
  • Dropbox Passwords autofills your usernames and passwords for instant access to your favorite websites and apps. You can sign in from anywhere with apps available for Windows, Mac, iOS, and Android.
  • The Dropbox desktop app runs on Windows, Mac and Linux operating systems. Apps are also available for iOS, Android and Windows mobile devices. And you can transfer and download files from dropbox.com using most modern browsers. For more details, visit.

Store all your work—like traditional files, cloud content, Dropbox Paper, and web shortcuts—right on your desktop. Easily find what you need using features like Starred files and folders, intelligently‐suggested folders, and image search.Included with Dropbox Professional and Dropbox Business.

Especially on the Mac, Dropbox handles these tasks in such a simple, transparent way that you can barely tell you’re using third-party software at all. It seems as if all you’re doing is moving items in or out of an ordinary Finder folder—except that Dropbox is far from an ordinary folder. Instead, it’s a special location that synchronizes everything in it with every other device, Mac and iOS, that’s logged in to your Dropbox account.

Perhaps you’re thinking that Apple’s iCloud, especially with its Documents in the Cloud feature, is an adequate alternative to Dropbox. Think again. As a result of Apple’s sandboxing and other self-imposed restrictions, iCloud lags far behind Dropbox.

On a Mac, you have no Apple-supported way to access iCloud documents from the Finder. Apple intends for you to access iCloud only via Open and Save dialogs. And it allows you to access a given document only from the Open dialog of the app that created it. So, if you use Preview to save a PDF file to iCloud, you won’t be able to locate or open the file in Adobe Reader. Even worse, if you want to view the iCloud-stored PDF file on your iPad, you can’t—because there is no Preview app for iOS that will show the file.

Apple’s iCloud setup means that you can’t group related iCloud-stored documents, created by different apps, into a single folder. iCloud also omits most of Dropbox’s secondary features, such as the ability to recover a deleted file or to share a folder with another user.

By accessing the hidden Mobile Documents folder where your Mac locally stores iCloud documents, you can work around some of these iCloud limitations. But this is hardly an ideal solution.

Apple’s perspective

By this point, you may well be asking: “Why?” Why didn’t Apple design iCloud to be more like Dropbox? Why isn’t it furiously working to redesign it now? Or why doesn’t Apple just purchase Dropbox and then either insert Dropbox features into iCloud or—at a minimum—leave Dropbox as a separate Apple-supported app. Either way, all OS X and iOS users would have instant system-supported access to Dropbox’s features.

Actually, Steve Jobs did try to buy Dropbox years ago, Dropbox’s owners say, and they turned him down. Still, we can fantasize about how wonderful it would be if, in a renewed effort, Apple could convince Dropbox to sell. Except that we would be wrong. The fantasy isn’t that Apple might someday acquire Dropbox; the fantasy is that its doing so would work out well.

The reason that iCloud doesn’t function like Dropbox is not that Apple’s engineers aren’t capable of doing a better job. Nor is it that they made decisions about iCloud’s design that they now regret. Apple knew exactly what it was doing and accomplished exactly what it intended. Apple doesn’t want iCloud to work like Dropbox. Instead, Apple is committed to a sandboxed approach that it originally implemented on iOS devices. Rather than loosening restrictions over time, Apple has extended sandboxing to Mac apps sold through the App Store. Limiting user access to where documents are stored and restricting documents to the apps that created them—this is all part of a deliberate strategy by Apple. Similarly, on iOS devices, Apple continues to prohibit users from installing apps that do not come from the App Store or accessing root level files; you need to jailbreak your device to gain such access.

Why is Apple so insistent on sticking to this restrictive approach? The consensus favorable viewpoint is that these prohibitions offer security advantages, better quality control, and a more consistent user interface. Whatever the reasons, limiting user access to software and hardware has been part of Apple’s vision from the earliest days of the Mac. The original Macintosh, in contrast to every other computer at the time, was designed so that the typical user could not open the case. Today’s MacBook Pros with Retina Displays continue this tradition. Kyle Wiens, of iFixit.org, has described them as “the least repairable laptops” he’s ever taken apart. While many view this negatively, it is consistent with viewing Apple’s devices as “consumer electronics” rather than “old-style computers.” After all, how often do you want to take apart your flat-screen television?

All of this leads me to conclude that, if Apple did ever buy Dropbox, it would kill Dropbox—after possibly retaining a few of its lesser features for iCloud. It would likely play out similar to the story of Apple and Lala.

Don’t worry

Still, I’m not losing sleep over this possibility. That’s because I don’t think it will ever happen. Apple knows that Dropbox isn’t the only game in town anymore. To be completely successful, Apple would need to start playing Whac-A-Mole, killing each competitor that ascended to replace Dropbox. Apple isn’t going to do this. So it will likely do nothing.

Apple is also unlikely to use updates to OS X and iOS to implement code that prevents Dropbox from working. Doing so would only drive angry users away from Apple’s devices and toward competitors that retain Dropbox support. Given that Dropbox isn’t going to be accepted into the Mac App Store anytime soon, Apple can at best simply hope that Dropbox use declines as users increasingly depend on the App Store for all their software.

The bottom line: Don’t expect a significant change from the status quo for the foreseeable future. That’s fine with me. I’ll take the status quo over the most likely alternative. But just in case I’m wrong, and someone at Apple is negotiating with someone at Dropbox even as I write this, I make this plea: “Stop what you’re doing. Now. Walk away from the table. Leave well enough alone.”

This is a story I never had any intention of writing. Dropbox updated its file-sync application for Mac last month, and the new version contains an annoyance that I would like to eliminate.

I figured this wouldn't be difficult, let alone newsworthy: I'd contact Dropbox, explain the problem, and find out if there's any way for me to change the annoying behavior. If there wasn't, I'd recommend that they make a small change to their app, and hopefully my message would be passed along to their development team and they'd eventually make a change.

Instead, I learned something both frustrating and fascinating: there are numerous Dropbox support employees who apparently have never used their company's Mac application and do not understand how it works. As a result, Dropbox's users have to explain to Dropbox employees how Dropbox's application works on the Mac.

As a division of labor, it probably makes sense for some support reps to specialize in Dropbox for Windows, or Dropbox for Mac, or Dropbox for mobile devices, etc. But when Dropbox rolled out a major change to its Mac application, it had support reps replying to Mac users without knowing what they were talking about. I don't blame the individual support reps—Dropbox the company needs to make sure its employees are prepared to answer user questions, especially in advance of major changes that will inevitably lead to a rise in user complaints. That didn't happen this time.

Dropbox Mac App

Dropbox wants to be front and center

To summarize, the problem is this: Dropbox now opens a new file browser and an associated Dock icon every time it starts, even if you don't want it to. If you're not familiar with Macs, the Dock is the line of applications on the bottom of the screen (or the side, if you've moved it in the settings) and serves the same function as the Windows Taskbar. If my computer restarts or if Dropbox restarts, the new Dropbox window that I don't want pops up in the Dock:

This isn't a huge deal, as I can quit Dropbox's new file browser and get rid of that Dock icon each time my computer starts up. I'm not going to stop using Dropbox—I've been paying the company $138 a year for 2TB of storage and for 12 months' worth of file history, which saves all deleted files and revisions to files. (It's going up to $158 next time I get billed, in February.) It's worth it to me because Dropbox still works great, while the alternatives have always been unreliable or disappointing in other ways when I've tried them. I'll get into that more later in this article.

But the Dock icon and window is a major change in how Dropbox presents itself to users. Dropbox has always been the kind of application that is there when you need it and gets out of the way when you don't. Dropbox's syncing and file-sharing features are integrated with the Finder (the Mac file manager), and there's a little icon in the Mac's Menu Bar at the top of the screen for when you need to change a setting.

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But now, Dropbox wants to be front and center at all times. The company built its own file browser to replace what's already available in the Mac Finder, and it opens that new file manager every time Dropbox starts. We wrote about it last week when Dropbox started rolling it out to more users. I've had it for more than a month since I somehow ended up in Dropbox's Early Access program.

You can use the Mac's Command-Q shortcut to quit the file browser, and the new Dropbox window and Dock icon will disappear—as long as you've also disabled the Mac feature that shows recent applications in the Dock. You can fix the other major problem by going into Dropbox settings and choosing 'Open folders in Finder' instead of 'Open folders in Dropbox.' That way, if you click the Dropbox Menu Bar icon and then click a file, it opens in the Mac's native file manager instead of Dropbox's own file manager. You have to change the setting because Dropbox's new app automatically switches the default from the Finder to Dropbox's new file browser.

Dropbox does keep syncing in the background after you quit the new file manager, and the useful Menu Bar icon will still be there. But you have to do this every time you restart your Mac, or every time Dropbox restarts. No matter what settings you choose, the new file browser and corresponding Dock open every time Dropbox starts. I suspect many people will just leave it in the Dock because they may not realize that Dropbox will continue running normally even if you 'quit' the file browser.

So what does this have to do with Dropbox support employees? Well, it turns out they don't know that it's possible for Mac applications to run without a Dock icon even though that's exactly how Dropbox worked for a decade. And they've been giving bad advice to users who want to change back to the old way of doing things.

Because multiple Dropbox employees are making this mistake, I assume this is a failure at a higher level. Dropbox made a major change to how its Mac application works, but it doesn't seem to have fully explained that change to its support reps. You'd think Dropbox would make sure its support reps have a baseline understanding of how its Mac app works and how the Mac Dock works before they have to respond to Mac users, but that hasn't been the case.

Explaining the Dropbox app to Dropbox employees

Check out this support thread that began a month ago with the title 'Can't remove Dropbox icon from Mac OS Dock.' The user who started the thread wrote:

On the Mac, in the past, I've liked just having a small discrete Dropbox icon on my menu bar to monitor things and then accessed my files from the Finder.

Dropbox on mac

After a recent update to the 'new' Dropbox, the Dropbox application itself now opens itself and slaps a big Dropbox icon in my Dock which I don't want there.

Trouble is, if I select to not open Dropbox on login, then the menu bar icon also doesn't appear and syncing doesn't take place at all.

How do I stop the Dock icon appearing on startup?

Dropbox Mac App Store

Thanks!

Pretty simple request, right? Except the Dropbox employee who responded told the user that it's impossible for Mac apps to not have a Dock icon, even though that's simply not true.

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The Dropbox employee responded:

[W]hile it would be worth noting that all active programs will appear on the Dock while they are open, kindly note that it will not be possible to remove it from there without removing the app altogether. From there, I've already made sure to note your thoughts in my report internally, since this would be some great feedback for our team devs.

The statement that 'all active programs will appear on the Dock while they are open' is false, as many Mac applications just appear in the Menu Bar and work in the background. That's how Dropbox worked until a month ago, that's how Dropbox's competitors still work, and yet some Dropbox employees think it's impossible. Many other Mac apps that can appear in either the Dock or Menu Bar let you disable the Dock icon, and Dropbox could easily do this by adding a checkbox to its app settings.

There's another strange response from a Dropbox employee in that support thread, in which the support rep suggests disabling Dropbox's ability to start up automatically upon logging in to the Mac. Yes, that would prevent the Dock icon from appearing, but it would also prevent Dropbox from working at all.

I contacted Dropbox on Twitter on June 13 and was told that there is no way to disable the launching of the Dock icon. The Dropbox employee who responded to me in that tweet did seem to understand the problem, but my further attempts were all answered by employees who don't understand how the Dropbox for Mac app works.

I contacted Dropbox by email on July 9, and an employee responded the next day with the following suggestion:

If I understand correctly, your current issue is that the Dropbox desktop application dock icon is getting in the way when using your device, is that correct?... As dock icons are associated to the settings on your Apple device, doing a quick internet search as to 'how to hide dock icons' might possibly yield the results you are looking to achieve.

How To Use Dropbox Mac

Similar to the Dropbox rep in the support thread, the Dropbox employee responding to me seemed to think that it's impossible for a Mac app to operate without a Dock icon unless a user finds some unsupported hack that changes how the app works. While it's possible to hide some Dock icons by editing each app's info.plist file, this didn't work when I tried it with Dropbox. And it's better for the app to support Dock hiding officially because a user messing around with how an app works can lead to unintended problems.

I responded to the Dropbox employee and explained that Dropbox never opened a Dock icon until recently, that there is no way for me to change how the Dropbox app works, and that Dropbox's development team should surely know that it intentionally made this change. I also asked the employee if he has used the Dropbox for Mac application recently because I wanted to make sure I could talk to someone who understands what the Dock is and how it works.

In his next email reply, the Dropbox employee did not answer whether he has ever used Dropbox for Mac. But, he told me, 'As you mentioned there is no way for you to hide the Dropbox dock icon, I have passed on your feedback to my development team for you.'