My Dropbox-to-iCloud Drive experiment has gone pretty well overall. Both were charging me $10 per month for 1TB of space, but now that I moved everything to iCloud Drive and pulled Dropbox back down to the free tier, I get to save $120/year.

For personal uses, iCloud Drive has performed pretty well for me the past couple months. The speed of saving files to and retrieving files from iCloud Drive feels on par with Dropbox on both iOS and Mac, thanks in part to improvements in macOS Sierra. However, I should restate that I do much less collaboration with raw files these days. I create and manage nearly all of my work in apps and services like Ulysses, Quip, Todoist, and Trello, then share or publish it with others in online systems like WordPress (this site), Weebly (my personal and business sites), Quip, or Google Drive. Of course, your mileage will vary.

The few raw files I still work with are things like PDF books I download, or media resources I snag from Unsplash, Envato, and elsewhere for content and blogging. If I need to receive files, I can of course still use my free Dropbox space, or I can visit Dropbox share links in a browser on any device. When it’s time to share files with others, Dropbox can still work, but so can Droplr.

Others who have made this transition told me there’s a noticeable performance boost to be had by uninstalling Dropbox from a Mac, which I just did yesterday. They weren’t kidding.

I’m pretty happy so far. I still use my Mac for a dwindling handful of tasks at least a couple times a week, so it downloads everything from iCloud (and still Dropbox) and backs up to my Time Capsule, just in case. But at this point, I’m feeling pretty good about simplifying my cloud services and saving money.

All that said, iCloud Drive is not without its drawbacks. Here are a few problems and speed bumps I’ve hit so far, and yes: I’ve filed radars (sometimes multiple) for all of these.


The ‘Save to iCloud Drive’ app extension is great, but

The “Save to iCloud Drive” dialog uses a terrible file viewer that is hard wired to 1) a list view, with no icon view option, and 2) have all folders and sub folders opened. It makes scrolling even a modest file library nearly unusable. I am quite disappointed that this shipped at all, especially since the iOS 9 app extension file viewer was much nicer. To work around this problem, I created an @Inbox folder on my Mac, which floats it to the top.

Oh yeah, folders

Update: Turns out I was wrong, you can create new folders in iCloud Drive for iOS. It’s arguably a little hard to find, but easy to use once you do. Tap the select button in the upper right, then a New Folder button appears with the other file management controls.

There’s no way to create a new folder on any iOS device. You need a Mac, because it is apparently still 2010.

Also, tags

Finder on the Mac has supported tagging files for a few years. While you can sort folder contents on iOS by these tags, there is no way to apply tags on iOS. You need a Mac, because it is apparently still 2010.

App folder clutter

All apps that store files in iCloud Drive are hard wired to have their own folders in the top-level directory. This means I have to scroll past folders for Byword, Cinemagraph Pro, Mindnode, etc. just to find my Documents or Resources folders. It would be great to have the option to collect those files in a specific folder, such as /Apps.

Restoring deleted files

This is a ding on both Dropbox and iCloud. iCloud Drive has what I think is a fairly standard a 30-day retention policy, kinda like Photos does for your media. But to restore files, you’re stuck like Dropbox: you need to jump on a Mac or PC to use the web interface. Also like Photos, this is functionality I believe should be built right into the app, especially since won’t let you get into any of the apps if you visit on an iOS device. While you can use the ‘Request Desktop Site’ option, I doubt it works well on iOS.


A while ago I got tired of suffering death by 1,000 clouds. I’ve canceled a couple of small services since then, but this is one of the largest changes and savings I can make. For my needs, it’s gone well so far, though I certainly hope Apple pays more attention to iCloud Drive to make it a more viable competitor in this space. Things like file sharing and competent file browsing tools are a must, and I’m hopeful Apple can close those gaps soon.

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