I’ve been using Dropbox for a number of years, but iCloud integrates better with my phone / ipad so I’ve just paid for the 50Gb storage option on that and want to switch across. I’m not ready to fully trust it though, and want dropbox as a backup.

My question is this: Can I keep the two synced together? I have a Dropbox folder on my Macbook in /username/Dropbox which auto-syncs to the cloud (via the dropbox app installed on my Mac).

I am aware that in the new version of OS X (Sierra, which is out in a week) iCloud will change and allow the ‘documents’ folder to be copied directly to iCloud. If I put my dropbox folder inside this documents folder, will this all play nicely? I realise that the services will only sync once my Macbook’s local folder has been updated (I.e. the Macbook is the ‘link’ and would need to be on).

Or is there another, smarter, way to do this?

I’d hold off upgrading to Sierra at the start until you understand exactly how the Home Folder > iCloud sync works out. I’d heard it doesn’t just copy the folder, but it completely moves it off your device and into the Cloud. How will you be able to access it when you don’t have an internet connection? What if your DB folder is in there too?

Dropbox will sync nicely on its own anyway, why bundle it with iCloud?

I’ve got 3-4 Gb of documents and other bits and bobs. I’d like the whole lot to be available from both services (Dropbox and iCloud).

Didn’t realise Sierra was going to introduce those changes. Surely iCloud will always keep a local copy?

From my reading the storage option to only store in the cloud and not locally only works if storage is low. It’s designed to be enabled if you are short on space on the local disk but isn’t the only option.

Sierra will sync your documents folder and desktop so just change your dropbox folder to be inside the documents folder on the mac and then they will both be in sync.

So predictably this was not as straightforward as hoped.

Mac OS X.11 Sierra just released, and the main change is much more streamlined iCloud integration which is what I wanted. However, if one copies the Dropbox folder into the iCloud documents folder, it just sits there and refuses to sync (the cloud icon gets a line through it to signify that it can’t be synced). I think this is something to do with the fact that the Dropbox folder isn’t a ‘real’ folder as far as OSX is concerned – It just tricks you into thinking it is.

However I think I have gotten around my issue with the use of Symlinks in the dropbox folder.

For anyone who stumbles on this and wants to know how it’s done (unlikely I guess):

Enable iCloud Documents sharing (in the iCloud pane of System Prefs)
Open Terminal and navigate to your dropbox folder
cd /Users/<yourname>/Dropbox

Then create a symlink here to link to the /Documents folder (which is now sitting happily in the iCloud)
ln -s /Users/<yourname>/Documents

Then drag everything from the Dropbox folder (apart from the newly-created symlink) into the iCloud Documents folder
The only problem with this is that Dropbox thinks everything is new (so it’s deleting everything in the cloud and re-uploading everything again) whilst iCloud is also simultaneously trying to upload the new 4Gb folder. So I’m basically uploading 8Gb until both services are synced and happy 🙄

Anyway, should be sorted by the morning 🙂