Wouldn’t it be nice to be able to edit the same files on your iMac and your MacBook without having to copy things back and forth manually? Apple’s iCloud Drive has made that possible for some time, but it was clumsy to store files in iCloud Drive instead of in your Documents folder or on your Desktop. No longer!
New in macOS 10.12 Sierra is Desktop and Documents folder syncing, which works with iCloud Drive to give you unified Desktop and Documents folders across all your Macs. Plus, you can access their contents on your iPhone or iPad using the iCloud Drive app! It’s easy to enable this feature, but be aware of the ramifications.
Before you begin, think about how much space you’ll need on iCloud Drive—add up the size of those folders on each Mac you want to sync. (If you have any Parallels Desktop or VMware Fusion virtual machines in your Documents folder, move them to another location because they’ll consume a ton of space.) If the total size is larger than the 5 GB of free space Apple gives all iCloud users, you’ll need to pay for more space: 50 GB ($0.99 per month), 200 GB ($2.99), 1 TB ($9.99), or 2 TB ($19.99).
Once you’re ready, navigate to System Preferences > iCloud > iCloud Drive > Options and select Desktop and Documents Folders. Make sure Optimize Mac Storage at the bottom of the dialog is not selected.
When you do this, Sierra moves your Desktop and Documents folders from your home folder to iCloud Drive, which could be disconcerting. They’re still accessible from a Finder window’s sidebar, from the Finder’s Go menu, and within iCloud Drive itself. It may take some time for iCloud to slurp up all your data, so be patient. For your other Macs, make sure they’re signed in to the same iCloud account, and repeat these steps.
From then on, when you create, edit, or delete a file on the Desktop or in the Documents folder on any of your Macs, Sierra syncs that change up to iCloud and then down to all your other Macs. It’s reasonably quick, depending on the speed of your Internet connection, but avoid working on the same file on different Macs without letting syncing complete first or you could end up with conflicted copies. If you’re offline, you can work as normal, but your changes won’t sync up until your Mac reconnects to the Internet.
If necessary, you can work with the contents of these folders on non-Sierra Macs directly in iCloud Drive—choose Go > iCloud Drive in the Finder to access them.
Some Sierra users have found that the contents of subsequent Macs’ Desktop and Documents folders end up in sub-folders named along the lines of “Desktop – name-of-Mac.” If you see this, make sure iCloud Drive has had time to upload and sync everything. If so, you can move the sub-folders’ files into the main Desktop and Documents folders manually.
Now, about that Optimize Mac Storage checkbox. When it’s selected, if your Mac runs low on drive space, Sierra may delete old, large files from the local drive to free up more space. The files remain in iCloud Drive, and you can click a cloud button next to their names in the Finder to download them. What’s unknown as yet is whether iCloud-only files will be backed up by Time Machine and other backup apps; you could end up with the iCloud Drive version of a file being the only extant copy. As a result, we don’t recommend selecting Optimize Mac Storage on your primary Mac, though it should be fine on a secondary MacBook with minimal storage.
Finally, if you decide to turn off this feature, Sierra creates new local Desktop and Documents folders in your home folder, but it doesn’t populate them with content from the previously shared folders in iCloud Drive. You may need to copy files from the iCloud Drive folders to the local Desktop and Documents folders to get everything back the way you want it.
Desktop and Documents folder syncing is designed to simplify the experience of using multiple Macs (and iOS devices!), but if you’re accustomed to each of your Macs containing different files, it may be more confusing than it’s worth.