Beware Desktop and Documents Folder Syncing on MacOS Sierra

Josh Marshall had a really bad experience with the new Desktop and Documents folder iCloud syncing feature in Sierra:

So today at work I had Sierra start syncing my work Desktop and Documents folders. Later I checked in iCloud and there it all was. Awesome.

What I didn’t see were my Desktop files from my home computer. That was odd because I’d upgraded to Sierra at home the night before. So why hadn’t it worked from home?

When I got home I checked to see if I’d enabled this syncing operation on my home machine. I hadn’t. So I checked the box to enable it. But when I did it said I had too many files or too many nested folders to use this service. I poked around on Google to find out about this because I hadn’t seen any reference to any storage limits. I couldn’t find any information about this. So I moved some files off my desktop to see if I could get under whatever this limit I was bumping up against.

After moving a bunch of files, I tried again. Success! It let me do it. Then in a flash all the files on my desktop disappeared and were replaced by the files from my work desktop.

It sounds like his files weren’t vanished — they were moved to a sub-folder of the iCloud Desktop folder. But it sure looked like his files were vanished. From Ars Technica’s Sierra review:

Enable iCloud Desktop and Documents on a second Mac you’ve upgraded to Sierra, one that already has files in its Desktop and Documents folders, and you will momentarily panic, as all of your existing files are removed and replaced with the “canonical” iCloud versions. But don’t worry; everything that was already on your desktop has been moved to a subfolder in the iCloud Desktop folder named “Desktop — [Name of Mac].” From there, move files around however you want to reconcile the desktops on your Macs. […]

It takes a while for your Mac to upload all your files into iCloud the first time you turn it on — the service seems reluctant to overload your Mac or to completely saturate your Internet connection, both of which can easily happen while syncing a service like Dropbox for the first time. Going to the iCloud Drive folder in the Finder will give you status updates as well as show you how much storage space you have left in your iCloud account.

So it’s not so much that the feature is dangerous but that the experience of enabling it on a second Mac is really poorly designed. When you enable it on a Mac when there’s already an existing iCloud Desktop folder, there should be some sort of dialog that explains exactly what’s going to happen.

★ Saturday, 24 September 2016