My iCloud Sync Failure Saga

🌳 Evergreen

It was mid 2019 and because my 2016 13” MacBook Pro was a secondary computer (to a 2018 Mac mini), I lasted only a few days past WWDC before installing the first developer beta of macOS Catalina. It was rough, to say the least, and many things didn’t work or only worked intermittently. Several betas later I noticed that my iCloud documents were not syncing from the laptop but, well, that’s what you get with betas, right?

It was after I had installed the final version of Catalina that I noticed my chosen writing app, Ulysses, did not seem to be syncing properly via iCloud. I got in touch with Ulysses support who worked diligently with me to identify that the problem was iCloud. Recalling the earlier issues, I looked more closely and discovered that original problem had remained, and I set about figuring out exactly what was… and wasn’t… happening.

I worked out how to precisely describe the aberrant behaviour, but not a single Apple rep spent the time to understand its literal meaning. I always had to explain it in some detail, anyway. But you, dear reader, will most certainly manage it… Any file that was created or modified on the MacBook Pro would never make it to the cloud, and thus other devices. Looking at it from the perspective of what did work, directories were fine, deletions of anything were fine, and any actions taken on any other device were fine. To put it yet another way, iCloud was syncing every which way as it should, except any content originating from the MacBook Pro. This did not affect all iCloud content, however. Photos, calendars, notes, and more would all sync just fine. It was only files in iCloud Drive, and some apps’ documents, including Ulysses but not KeepIt. The difference between these apps is in how they use iCloud — the old way (Ulysses) or the new way (KeepIt).

On 26 November 2019 I reported the problem to Apple. I quickly made it to the first of several Senior Advisors who would take me through a series of troubleshooting steps. This basically consisted of an endless series of questions and instructions on gathering copious logs and recreating the problem with while noting precise timings and taking screen captures, all to be sent to “Engineering”. After spending from 15-60 minutes on the phone with a Senior Advisor, I’d be lucky to get a call back several weeks later asking me to do it all again but slightly differently. If I was unlucky I’d get no response and I’d have to call them back after 3 weeks or more, at which point I’d get a new Senior Advisor. At one time an advisor promised to call me back but instead left the company and failed to hand over my case to anyone! On the 27 March 2020 — four months after I reported the issue — I got several messages saying Apple tried to call but I had not answered my phone. Well, that’s because it never rang1. When my attempts to follow up on this met with silence, I gave up. I wiped the laptop, sold it, and bought an iPad Pro to replace it. This completed phase one of the saga. I was rid of the cursed laptop and every device I then owned synced perfectly. I had won the battle. Or so I thought.

It is important to note here that among the troubleshooting steps I performed with the laptop were three complete wipes of the laptop followed by internet installs of macOS — both Catalina (twice) and the laptop’s original OS, High Sierra — and the problem persisted every time in identical fashion. This is part of why I gave in and got rid of the laptop. Like a cockroach, the issue survived even the nuclear option.

From May 2020 I hugely enjoyed my 11” iPad Pro with Magic Keyboard. It was fantastic for writing (Ulysses worked very well on it), superb for TV watching (I watched the entire run of Long Way Up on it — stunning visuals!), and pretty decent for most other things. But… I couldn’t fiddle with Xcode. I couldn’t use my preferred photo processing software. I often hit the “iPadness” of iPadOS that just makes some tasks that much harder. For instance, I could never get the hang of the Affinity Photo interface on iPad. I’m just a Mac person at heart.

So… when the Apple Silicon Macs were announced in November 2020, I decided it was time to ditch the iPad Pro lifestyle and return to the fold with a new 13” MacBook Pro. This laptop is everything I hoped it would be. It’s incredible. I charge it like I charged my iPad. Overnight. It’s fast. The keyboard is superb. The screen is gorgeous. My photos really pop, and I’ve watched the entire first season of For All Mankind on it.

So… imagine my horror when I realised a couple of weeks after making it my primary Mac (with the 2018 Mac mini eventually sold as the M1 runs rings around it), that “files which are created or modified” on my brand new M1 MacBook Pro, running Big Sur, do not make it to iCloud. It is exactly the same problem. Different OS, different laptop, same problem! I actually felt slightly sick on the realisation it was back. Phase 2 had begun.

A little over 13 months after originally reporting the problem, I reported it again on 30 December 2020. I had a few different Senior Advisors again, but all of them were great (no-one has left the company that I was aware of!) and they all listened to my pleas not to go through ALL of the troubleshooting done the first time around because it must surely be a problem with the iCloud servers. I collected logs and screen captures once and I was called back within reasonable timeframes. Every time I spoke to a Senior Advisor I pleaded my case to get someone to look at the servers. I think it wasn’t really going anywhere again2 until I got frustrated and decided to do some of my own digging.

From searching Google I had learned some details of iCloud processes that run on macOS so I opened the Console app and started looking to see what the logs would reveal. I couldn’t make head nor tail of most of it, but decided on an experiment. I set a filter to only show the one iCloud process and waited on it to stop spewing messages, then cleared the log window. At a precise time I created a new file by means of a screen capture which was saved on my Desktop (being part of iCloud Drive). More messages spewed forth and when they stopped arriving, I copied all of them out to a text editor and started to study them.

I was able to locate messages relating to the syncing of my new file being attempted, and of the sync attempt not failing but being re-queued for later, then nothing. I repeated the experiment and found exactly the same pattern. On 7 March 2021 I sent a detailed email to Apple Support with what I’d done and what I’d found. I got a call from my Senior Advisor who made sure he understood what I had sent and then forwarded it to Engineering. Two weeks later, my Senior Advisor called unexpectedly. He had news from Engineering. I steeled myself for disappointment but inwardly I was hopeful.

“Engineering have identified the bug. 😯 They have said there will be a fix. 🤭 But they cannot say when that fix will be released. 😶”

I had a bit of a fruitless conversation with my Senior Advisor about what this meant. In short, every time a new macOS release is published, I would be hoping it fixes my problem. It was not in 11.3 nor 11.3.1, nor 11.4, 11.5, 11.5.1, 11.5.2, 11.6, 11.6.1, 12.0, 12.0.1, 12.1, 12.2, and 12.2.1. You can imagine, as each release arrived without a fix, what little hope I had was slowly eroded. I began to install new releases with the solid expectation that nothing would change. And nothing did, until March 2022 when 12.3 was released.

As usual I set about installing 12.3 soon after it was released. There was only a hint in the back of my mind of the low-to-no expectation that iCloud would magically spring to life. I ran the install while I was reading in bed one night. The next day when I plugged it into my OWC dock, Spotlight went to town re-indexing… something… and as a result the computer was quite unresponsive. While it was in this state, I noticed something unusual. iCloud Drive showed the little progress pie chart in the sidebar. I hadn’t seen this for months. Had something changed? I waited for the CPU to calm down, but my Magic Trackpad was still jumpy, so I restarted the laptop. When I logged in again, the pie chart was gone. How intriguing! I decided to look inside iCloud Drive and got a surprise!

There were no cloud symbols anywhere. These had become a permanent fixture on some folders, plus I had left some of the test files there for a reason I cannot now explain. Everything reported as synced. Then I spotted a large (55 MB) file I knew I had created only days previously. It had no cloud symbol. Could this be it? Was it finally working? I pulled my iPhone out of my pocket and trepidatiously opened the Files app. I could see the 55 MB file!

It took me a few days to accept that any and all files were now syncing as they should. My saga was finally over, and it only took 842 days from my first report to Apple.

But there is a twist to this story. For a time, I was using my Mac mini to effect iCloud uploads that were stuck on the MacBook Pro. This involved setting up a folder on the Mac mini which I then shared on the network. Stuck files were easy to identify on the MacBook Pro as they had an iCloud symbol next to them and usually an arrow indicating they were currently uploading. They weren’t, of course. Carefully, directory by directory, I would move these files out of iCloud on the MacBook Pro and into the network share on the Mac mini, and then on the Mac mini I would move them into the correct iCloud folder again. Moments later, the files would re-download on the MacBook Pro. A fiddly process, but it worked. Until I decided there must be a way to automate this.

It turned out to be quite simple, if a little complex on syntax. I built a Quick Action on the MacBook Pro using Automator, which I titled “iCloud Fix”. This action moved the file to the network share and renamed it so the file name includes the entire original path. On the Mac mini, Hazel watched this folder and by means of a shell script, decoded the file name back to the path and the original file name and moved it back to the correct location in iCloud. The net effect of this was right-clicking a stuck file and choosing “iCloud Fix” caused the file to temporarily disappear and then reappear, correctly synced to iCloud, and thus all my other devices. It could be done on one or many files and in any iCloud directory, it’s relatively fast, and it’s not fiddly at all.

Screen capture of the iCloud Fix Quick Action in operation.

On a final note, the hugely repetitive gathering of logs and other details that I had to do with Apple the first time around, with no real payback, made me think of a passage from my favourite book, The Hitchhiker’s Guide to the Galaxy. In reference to the Vogon race, The Guide had this to say.

They wouldn’t even lift a finger to save their own Grandmothers from the Ravenous Bugblatter Beast of Traal without orders signed in triplicate, sent in, sent back, queried, lost, found, subjected to public enquiry, lost again, and finally buried in soft peat for three months and recycled as firelighters.

The Automator Quick Action script (Workflow receives files or folders. Pass input as arguments):

for f in "$@"
  mv $f /Volumes/macminiusername/tempicloud/$new_name

The Hazel script for watching tempicloud (match on file starts with %):

input_leaf="$(basename "$1")"
mv "$1" "$old_name"

  1. On a call for the second reporting of the issue, an Advisor told me there was a known issue calling from the US to other countries that resulted in this exact scenario. It seems like a known issue should be… known.
  2. I was offered the option of “resetting” my iCloud account, but I was not keen on that option because it’s REALLY hard to figure out all the iCloud data that is NOT in iCloud Drive, which would all be lost. How do you back up that which you cannot identify?