Moving from Dropbox to iCloudDrive - multiple macs

OK - so I would like to make the move from Dropbox to iCloudDrive for my document storage.

At the moment the documents folder on my home computer is connected to dropbox via a symlink (thank you macdropany!) I also have a laptop and a mac at work, connected to the same dropbox account, which means that the documents folders on each computer are all kept in sync. It has worked faultlessly for a number of years.

So how do I do this using iCloudDrive? If I check to sync the ‘Documents’ folder on each machine, then I get 3 documents folders on my iCloudDrive. I have read that I can drag them into each other to merge them, and this will then keep them all in sync.

Is this correct?

Thanks in advance for any help.

God bless,


There are several ways to do it. I think I would turn off Dropbox sync, move the files on one of the Macs off to the side (outside of iCloud’s area), then enable iCloud sync on the first Mac with your documents in the normal iCloud location. And of course enable iCloud sync on the other Mac as well. This way you have a copy of the Dropbox versions as a safety net while letting iCloud sort out syncing in the normal way. It means one of the Macs has to download all the files but ISTR this is the approach I took when I migrated and it felt safe and was trouble free.

FYI today Appleinsider posted an excellent overview detailing the ins and outs of file storage on iCloud.

According to this article, which was written just today, Apple creates new desktop and documents folders on your Mac entitled “Documents - Mac Name” or “Desktop - Mac Name”. It also mentions that when you turn on iCloud sync your desktop and document folders disappear from your Favorites in the finder sidebar.

Neither of these are visible to me. I do not have such a folder on my desktop. And both my desktop and documents folder appear in my sidebar.

I have been using this feature since it was released and it has worked flawlessly. I have full access to my client files stored on my Mac even out in the field using my iPad. My documents folder is not huge, but it does have a lot of files—24GB with about 22,000 files.