What to do when iCloud gets stuck

Another great article from Howard Oakley, which I am posting because the topic arises so frequently here. Be sure to read the comments, there are a couple of valuable tips there


Excellent advice from Hoakley. His utilities are very good too.

A great article, and after reading it, and especially this:

For this and other reasons, I still urge users not to enable Desktop & Documents unless their Documents folder is going to remain small, perhaps by adding a local folder to their Home folder for locally stored documents only, which defeats the purpose.

After reading this whole article, I disabled Documents & Desktop sync everywhere.

iCloud works great for almost everyone. However, the lack of diagnostic tools mean that if you run into problems, there’s very little you can do other than turn it off and turn it back on again and hope it works.

For all Dropbox’s problems, it’s much easier to see what’s happening than iCloud.

I keep this turned off on my Mac too. A few years ago, in the early days of Desktop & Documents sync, my VP lost all her files when this got turned on. Fortunately I ran daily backups on all executive Macs and was able to restore everything.

That’s no comfort for the people who lose their data playing iCloud roulette. IMO Documents & Desktop sync is a feature that should be used only by power users who understand the risks. It’s not something that should be turned on by default.

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Luckily, all I ever lost was a couple of hours of highlighting and annotating a single PDF file that was in an iCloud folder (I was experimenting with Bookends in macOS/iOS, which relies on iCloud). After that, I went back to Dropbox and bid iCloud and Bookends farewell.

For those still having troubles with iCloud, don’t forget to check out Howard’s Cirrus.

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Thanks for this, it makes an interesting read though I think does nothing for my particular situation. I know iCloud won’t upload files from my MacBook Pro. It hasn’t for two years. But turning off Documents and Desktop doesn’t really solve anything for many people, other than perhaps save you from a complete catastrophe that may befall later.

I’ve been having a looong dialogue with Apple over my iCloud problem (chronicled elsewhere in these forums) and just recently I ended up with a really attentive and perceptive Senior Adviser. He’s a fellow Antipodean, so of course I expect the best from him. :wink:

Anyway, we got talking about a prior offer made by “Engineering” to perform an “iCloud Drive Reset.” I had a wee bit of a rant to my new best friend, though was respectful that none of it was his doing. When I got to the end and gave him enough leeway to say what he thought his first words were along the lines of “I see what you mean.”

Previously, when I was offered the reset, I was sent a link to a “how to back up iCloud Drive” support document. Which is basically teaching me to suck eggs (hint: copy the files somewhere) but at the same time does not explain how to back up everything in iCloud Drive. It was this last point my new friend said “good point!” to and he then went and asked Engineering about it.

If you think you know what gets stored in iCloud Drive (or at least could if you let it), pop into System Preferences and click on the Apple ID icon at the top. Then, click on the Options… button next to the iCloud Drive entry.

Many will already appreciate the “iCloud” is a superset of “iCloud Drive” as did I, but I was surprised to learn that everything in the list behind that Options… button is storing data in iCloud Drive. Including, for one example, Messages. I asked a previous Senior Adviser and she was surprised by this. I said “is that all my message history that I have sync via iCloud?” She found a support document that said no, it was the attachments people send you in Messages. So when your significant other sends you that photo of the cat sleeping upside down, that photo is stored in iCloud Drive (possibly only true if you sync your Messages through iCloud).

How about Maps? Yup. It’s listed as storing something in iCloud Drive. I know not what! I have asked and my Senior Adviser asked Engineering who, frankly, missed the point the first time, so I had him ask it again and they’ve now come back to him and said “Good question! We’ll need to research that.” So even Apple’s own iCloud engineers don’t know what’s stored in iCloud Drive.

Then I went further and asked “how do I determine what third party data is in there?” I know for a fact that if you tell Ulysses to store and sync its content in iCloud it uses iCloud Drive. I know this because it was this application that first alerted me to my problem a couple of years ago. But I also know that KeepIt’s iCloud Sync does not use iCloud Drive because it has worked absolutely perfectly the entire time. Engineering were also referring to this in their “good point!” response.

The next question they did not have a ready answer for is if they nuke my iCloud Drive (which they have said will remove all content from the server and that will in turn remove that content from every device), will a restore from Time Machine on my Mac actually put all iCloud Drive content back and thus propagate it to the cloud?

I got an update from my Senior Adviser that he’s still waiting on Engineering to come back with a response to these questions.

So turning off Documents and Desktop, as I mentioned, will save those files from a fate worse than cloud, but there are potentially other apps you use which will also suffer the curse, and yet, some will not. And you won’t know which until something breaks and you won’t know what to back up or how.

Finally, if you think you can figure out what Maps is storing in iCloud Drive (I do have one guess) then here’s another one to wrap your head around. Also listed in the iCloud Drive list of apps is… System Preferences!