Folder sharing brings iCloud Drive closer to Dropbox, but there’s work left to do

Last year, Dropbox revised its terms so that free accounts, like mine, could only sync data with up to three devices. As someone who owns an iPhone, iPad, iMac, and MacBook Air, I was a bit put out by this change: I kept all my important files in Dropbox and relied on its syncing magic to have access to that data no matter which device I was using.

This wasn’t my first frustration with Dropbox, which has started focusing more on enterprise software rather than its core functionality of document sync. So I decided to bite the bullet and make the switch, moving to iCloud Drive for all my cloud storage needs.

Overall, the transition has been largely smooth, but it has put into relief a few places where iCloud Drive currently just can’t match Dropbox. One of those features, the ability to share folders, looks to finally be arriving in iOS 13.4, the beta of which was released this week. But before I’m finally able to kick Dropbox to the curb, there are a few more tweaks that iCloud Drive needs.

File under “request”

One feature that Dropbox has had for some time is the ability to create a file request. This allows users to turn a folder into someplace where anybody with a given URL can upload a file via a web interface.

In my line of work, I use this feature regularly in order to requisition files from guests on my podcast. It’s far simpler than setting up a shared folder for all of these uses, which involves doing the dance of making sure the participant has a Dropbox account, sending them an invitation, making sure they accept it, and then hoping they remember to drop their file in the correct place. Plus, using a file request link means I don’t have to worry about managing a potentially large number of users with read and write access to a folder.

This feature doesn’t even seem to be on Apple’s radar, and that’s not a surprise: I imagine this isn’t even a hugely popular capability for Dropbox. Apple has also never been the most web-savvy of companies, so a web-based upload tool probably isn’t high on the company’s list—especially when it’s still struggling to implement shared folders.

But there would be benefits in Apple implementing such a feature, not least of all because it would help make iCloud more platform agnostic, allowing users on Windows, Android, or even Chromebook devices to easily upload files to iCloud. And given that Apple just this week deployed a mobile-optimized iCloud.com that made the service more accessible on both iOS and Android devices, it seems like platform interoperability is at least of some interest to the company.

Old reliable

My experience using iCloud Drive has been pretty solid so far: on the Mac, I’ve run into very few problems accessing my files or moving things into and copying them out of iCloud Drive.

However, on iOS, the story hasn’t been quite as positive. Apple has spent several years trying to figure out how to implement a file system on its mobile platforms, given those devices were never really intended to deal with files in the first place. But while the latest version of the Files app is surprisingly capable, I’ve still run afoul of more than a few reliability problems.

The biggest one for me is that for some reason, files will sometimes just not load. I’ll tap a 300KB spreadsheet that ought to open immediately, and instead a loading icon will spin interminably. Sometimes there’s no fix beyond rebooting the entire device and crossing your fingers. Other times, I go to save a file in iCloud Drive from an app like Pages, and I get stuck at an unresponsive or glacially slow file browser, as though Open/Save dialog boxes haven’t existed on Apple devices since time immemorial.

This shouldn’t be the case: iCloud Drive needs to be absolutely reliable if the company wants users to depend on it. One of Dropbox’s great innovations was that it acted like any other folder on your Mac, making its use entirely transparent. Drop a file in, and you could be assured that file would be there, just like any other file in any other folder. iCloud Drive, meanwhile, still feels like a special, cordoned-off area of the file system. With the kind of deep access Apple has to its operating systems, it seems as though the company should be able to integrate it seamlessly—but the cracks definitely show.

Spacing out versions

I’ve mentioned it before, and I’ll no doubt mention it again, but Apple’s inclusion of a mere 5GB of storage for iCloud storage—all iCloud storage—is miserly. Sure, it might seem like more than the 2GB Dropbox offers for its base tier, but keep in mind that the 5GB also needs to accommodate your email, any photos stored in iCloud, device backups, and more. That space gets eaten up pretty quick.

If Apple is serious about iCloud Drive being a real replacement for something like Dropbox, it ought to beef up the storage space it’s providing. It’s not so much for serious users, who are probably going to end up buying more storage anyway, but for casual users who probably won’t bother using the service if they are worried about running out of room.

And while the company’s at it, it should expand access to previous versions of documents. If you’re using apps like Pages, Numbers, and Keynote, you can access versions of documents stored in iCloud Drive. Even if it’s not a true cloud backup, it at least provides a safety net for users of the service, which helps it feel more secure.

Update, 2/14/20: An earlier version of this article stated you could only access previous versions of iWork documents via the Mac—but they are also accessible on iOS.