Question about Documents in iCloud Drive

When “Desktop & Documents Folders” in iCloud Drive’s options is checked in Mac 1, does it mean that in Mac 2 the contents of Mac 1’s Documents folder will automatically appear (and be in sync on both the computers) when “Desktop & Documents Folders” in iCloud Drive’s options is checked?

What will happen when on Mac 2
a) Documents folder is empty
b) There is different content in Documents folder already present.

i.e., does it behave similar to a folder that is placed inside the “iCloud Drive” folder?

If one computer’s folder(s) are empty and you turn this on, it simply copies from the cloud to the empty computer.

If the folders have different contents, it attempts to merge and asks you about conflict. If needed, it will create a “COMPUTER NAME Desktop” folder so you can be sure to know what the source of those files was.

I’ve found this to be rock solid over the last two years and have never lost a file with this setting on. (And I move between computers / set up new ones often!)


The two Documents folders on the different machines will be merged into the iCloud Documents folder and that merged folder replicated to both machines. I don’t remember how conflicts are handled. It works great for me with an iMac at home and an Air for traveling. I always have all,my documents on both machines in sync.

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Thanks for the replies.

I am trying to decide between having all my files and folders inside the “iCloud Drive” folder vs inside the “Documents” folder (and then checking this in the options).

What I don’t like about the former is that there are a number of App-specific folders already present and doesn’t look tidy.

Would you be willing to share with us the approximate size of your Documents folder (# of files and how many GB)?

Are there any problems or delays/downtime when you need to sign out of iCloud, then sign back in, for some reason?

The other advantage of using the Desktop/Documents option is that those folders are always in favorites lists and sidebar shortcuts on iOS and Mac. I switch from Dropbox to iCloud Drive for my desktop and documents folders a couple of years ago and the whole experience has been great.

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You didn’t ask me, but I’m in the same boat, so I’ll answer.

Documents folder is 38GB, roughly 13,000 items.
I’ve never had any issues with this feature (compared with iTunes Music/Match, iPhotos, Messages in the Cloud, etc. which have all been rather flakey).

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Items placed in regular iCloud Drive folders are synced to each Mac. The reside on your local drive and the cloud and will be backed up the same as any other file on your drive.

Items managed by the Desktop and Documents feature may or may not reside on your local drive at the time your backups run and are therefore, IMO, not as secure as local files or files in iCloud Drive.

Documents is 263k items and 97gb of space. Photos library is 22gb for 10k photos.

Haven’t really needed to signout for any problems. When I setup my new iMac I copied the Documents folder from my backup so all iCloud had to do was verify the syncing. Left it alone while I did other stuff. Don’t know how long that took. When I was on a slow connection syncing could be painful but I now have a 950/30 connection so it goes fairly quickly. My iMac usually sees 600/30 speeds.

I have now fully moved from Dropbox and pCloud to iCloud Drive. Subscribed to the 50 GB plan.

Originally had all my stuff inside a folder by my name in the iCloud Drive folder, but decided to move that to Documents folder and have “Desktop & Documents Folders” synced.

Next is to understand how Photos work deeply. Might purchase Photos Field Guide (2nd Edition) | MacSparky Field Guides.

Let me know how that goes. I’ve been wanting to make the jump. I keep my photos on a personal Smugmug site for the last decade and would love to have one less bill and one less thing to maintain.