Successful iCloud Desktop and Documents Folder Storage
This article tells the story of what happened after I turned on iCloud Desktop and Documents Folder storage in the iCloud pane of System Preferences, shortly after installing macOS v10.12 Sierra on my Mac Pro (Late-2013) and my MacBook Pro (Late-2013). My aim is to help others to feel comfortable doing it themselves while avoiding the pitfalls I discovered along the way. I include a lot of detail here, most of it not yet mentioned in other online commentaries. The process took a few days and was full of unexpected turns and hard decisions, but it came out well in the end. I can now happily use continuity, switching freely between my two Macs, my iPhone and my iPad, editing the same document on all of them.
Previously: macOS 10.12 Sierra Notes.
Update (2016-09-27): Rich Trouton:
Based on the results of my testing, I have no plans for enabling iCloud Desktop and Documents syncing on any of my Macs for the foreseeable future. Leaving aside that Apple isn’t offering enough storage space at prices I want to pay, the results I saw from my testing of the synchronization process did not inspire my trust in it.
It did give me an insight into why Apple chose to remove support for portable home directories (PHDs) in Sierra. The havoc that could be caused by two separate synchronization processes trying to sync the same set of files, especially when portable home directories were using a two-way sync process, would be breathtaking to behold.
But Mac users may also be running that same risk without even realizing it. Because that first option – to ‘Optimize Mac Storage’ for files stored on iCloud – is on by default in my experience. This means that, for any file on iCloud, your Mac could be deleting files from your Mac without your knowledge or permission. That should never be the case.
It should never be the case for safety reasons, but also for reasons of practicality. We don’t all live in an always-connected high-speed Internet world, where we can access any cloud file simply by waiting a few seconds. Many of us frequently work on the move, on trains, planes and metro systems where Wi-Fi is either unavailable or exceedingly slow and unreliable. This is not the time when you want to discover that the document you want to work on doesn’t exist locally.
So it’s not so much that the feature is dangerous but that the experience of enabling it on a second Mac is really poorly designed. When you enable it on a Mac when there’s already an existing iCloud Desktop folder, there should be some sort of dialog that explains exactly what’s going to happen.
Update (2016-09-28): Phil Stokes:
I then re-enabled iCloud in the hope that this would refresh whatever it was that had become out-of-sorts. Unfortunately, that still didn’t work. I next tried unlinking again, logging out and re-linking after logging in. Still no dice, and by this time I was sufficiently worried that there was nothing for it but to halt all my other activities on the computer and try a restart. Possibly the system holds something in a memory cache that needs to be flushed, I’m not sure. In any case, I took the step of unlinking iCloud first, then restarting, then re-linking after reboot. Success (and relief)!
Update (2016-10-30): Lloyd Chambers:
If your data is moved into the cloud by iCloud Drive, it means that your local backups won’t be backing up your crucial data. Which means there is only one (1) copy of your files, eg. NO BACKUP at all. Just iCloud as the sole copy (presumably Apple backs up, but do you really trust Apple that much?)
