I have an incredibly annoying iCloud problem that Apple seem incapable of fixing (if they’re even trying). I’ll spare you the rant (well, mostly) that I’d love to make about trying to get Apple to sort it. I am hoping the clever hive mind here can suggest some things I haven’t tried.
I have a MacBook Pro (MBP), Mac mini (MM), iPad mini, and iPhone 11 Pro. The Mac mini is on the latest Catalina version, the others are all on the latest current OSes, though as I will explain the releases are probably immaterial.
I have iCloud Drive turned on everywhere, and I have “Store Documents and Desktop in iCloud” turned on on both Macs.
iCloud Drive works flawlessly, except: Any file that is created or modified on the MBP will not be synched up to the cloud. If you change any of the bolded terms, it works fine. Folders can be created, changed, deleted anywhere and sync everywhere. Files can be deleted anywhere and sync everywhere. Files can be created or modified anywhere except the MBP and they sync everywhere including to the MBP. “Anywhere” includes iCloud Drive on the web (including on the MBP). The successful syncing of any of the ones that work occurs in ~5 seconds to all devices. It seems the issue lies in the MBP sending data to iCloud. And when it “fails”, it usually looks like it is constantly trying but it never actually gets anywhere. I’ve even left it untouched for >24 hours and still nothing.
Here’s the fun part where I tell you what I have already tried, or at least, what I know doesn’t work. Obviously the focus is entirely on the MBP.
Formatting the SSD and reinstalling the OS does not fix it. Installing a different version of the OS does not fix it. Turning iCloud Drive off and on does not fix it. Turning iCloud Drive off for >24 hours then back on does not fix it. Changing networks (wifi in multiple locations plus Ethernet at home), uninstalling VPNs, starting in Safe Mode, and booting off an external drive do not work. Selling the laptop and using an iPad for 6 months, then buying a completely new laptop that uses a different CPU and an OS you’ve never touched before does not fix it!
OK, I should explain that last bit. I originally hit this problem with a 2016 MBP I bought refurbed in 2018. It happened late in the Catalina beta cycle and never went away through all of the above machinations, most of which were at the direction of Apple Support/Engineering. I even installed High Sierra (original OS for the laptop) and it was still there. After four months of no more than this (seemingly endless) basic troubleshooting and (seemingly endless) log collections, it was going nowhere and I gave up when Apple claimed they tried to contact me but my phone never rang. I wiped and sold the laptop and bought an iPad Pro.
Life (and iCloud) was great until the M1 Macs landed. I couldn’t resist. I sold the iPad Pro and bought an M1 MacBook Pro (now taking the MBP role in this story). After days spent setting it up as my primary computer (taking over from the MM) I realised the problem was back! And it is exactly the same. I had told an Apple Senior Adviser previously that I thought the problem surely had to lie in iCloud itself but he told me I wasn’t correct in that assumption. I think I am vindicated now! (Though I am flummoxed as to how it does not affect my Mac mini!)
I also found a few incantations that involved terminal commands and careful sequencing of steps to try to force some iCloud process to “re-evaluate” but nothing has worked. The problem maintains its exact same behaviour.
It’s one thing to use the MM as a workaround to get the files in the cloud, but apps like Ulysses are affected too. I basically cannot use Ulysses on MBP without resorting to “outside of iCloud” files, which lose me both the simplicity of Ulysses and some features. I opened a new call with Apple in December, but after a month with no response to my last email I rang Apple again earlier in the week and managed to get an update that “they’re still investigating” but I just don’t believe that’s true any more. I have another call scheduled in a week on which I expect to hear the same.
Hive mind, what can you suggest that I may have missed? Turning anything off and on has already been tried. I have already refused to do those actions again with Apple on account of all I did last time and the identical nature of its reoccurrence. It would just cause me more effort for, I am certain, no gain.