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I have a mac book pro which I enabled syncing desktop and Documents to iCloud.

This is working fine.

I also have a iMac which has a different desktop and documents.

If I also enable syncing desktop and documents to iCloud on the iMac.

Does it separate the documents & desktops into different folders on iCloud.

Or

Does it merge the two together into one desktop and one document folder.

If it merges, what does it do with files and folders that are the same name but different documents?

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My understanding is that there is only one desktop synced per iCloud account. I would remove everything from the desktop of an 'about to be connected' mac - so you can manage any clashes.

Add your Desktop and Documents files to iCloud Drive says

You can organize and combine folders from multiple Macs when you turn on Desktop and Documents on those computers too. After you turn on Desktop and Documents on a second Mac, you'll find its files in folders with the same name as your second Mac inside your original Desktop and Documents folders. Then you can combine your files manually, but iCloud doesn’t automatically merge the files in case you want to keep them separate. Any edits you make are seamlessly updated in iCloud Drive. There’s no need to manage your folders and files again on your other devices.

  • If you look at the graphic supplied with the above explanation from Apple it seems to indicate clashing files will be placed in a distinct folder on the merged desktop. – Michael Rourke Oct 18 '17 at 2:25
  • I ended up moving all the files on the second desktop/documents into a uniquely named folder, and then let it sync, that synced across fine, so now the two computers are in sync with each other. – Charlie Smith Oct 19 '17 at 1:31

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