How a Strange Mac Bug Took Up a Ridiculous Amount of My Time
I had all these plans for a series of posts on the blog last week, and even a video I wanted to shoot, but instead I ended up spending an inordinate amount of time chasing down a bizarre Mac bug. It seems to have resolved, but the cause still eludes me. It started with a Lightroom crash, and ended up leading to a complete puzzle that plagued both my Mac Studio and my MacBook Pro. It involved several calls to Apple and even baffled them. This might not sound like a riveting read, but it’s actually a curious tale and I learned a few things along the way.
So buckle up…
It started with a crash
While some people like to complain about Adobe apps and their stability, the truth is, I never really get many crashes. Lightroom almost never crashes, and even After Effects (a crash happy application if there was ever one) is relatively stable these days. So I was quite surprised when in the middle of working with Lightroom the application hung and presented me with a strange dialog box I had never seen before. I didn’t get to screenshot it and I partially ignored it but it was something to do with syncing or core sync or something.
I had been having a few issues with the creative cloud app and had recently reinstalled it, so I figured that was the culprit. Except it wouldn’t even launch. Nor would any other Adobe app.
Curious.
I went to go online to look for answers or at the least re-install the creative cloud application, except I couldn’t go online because safari was saying that iCloud private relay was unreachable. Now this isn’t the first time thats happened, and normally it just reverts to a normal connection.
Odd I thought, and went to disable iCloud private relay.
Except I couldn’t.
In the system preferences, its status was listed as “unknown” and you couldn’t change the state. Strangely enough though Chrome still worked, and was able to access the Internet without any issues.
Even more Curious…
Thinking it might be a weird router issue I rebooted the router and my cable modem. No luck. So I rebooted my Mac and after it came back up I was able to turn off iCloud private relay. Everything seemed ok for a while until I noticed that images weren’t loading in mail.
“Ok, this is getting weird”, I thought.
So once again, I checked to see if iCloud private relay was the issue, and that maybe it had somehow turned back on, but again the status was “unknown”. Again I rebooted, and once again everything was back to normal….for about two hours when the same thing happened again. I was getting frustrated at this point as having to regularly reboot is a total pain when you’re working on something.
Et tu Macbook?
It was at this point that I got out my laptop to work on that so I wouldn’t be interrupted while I tried to figure out what was wrong. As soon as I opened the lid and tried to go online I got the same error message about iCloud private relay. It was having the same issue with not being able to turn it off unless you rebooted. So I figured as it was happening on two machines at once, it must be either a remote server issue or a software bug.
Both computers had recently been upgraded to the latest version of MacOS at the time so I thought maybe there was a bug? I had updated shortly before it started happening on my Mac Studio so it seemed like a reasonable hypothesis. Either way it was becoming a real problem as it was taking up too much of my time.
Luckily I have Apple Care on my Mac Studio, so it was time to call Apple.
The 7th Circle of Apple Care
If you’ve never had to dal with Apple Care before, count yourself lucky. It’s kind of like going to the ER. You start with triage through the chat system, and then gradually your case gets escalated to more senior personal. No matter how hard you try you can’t go straight to a senior person. The other frustrating thing is that they treat everyone like they know nothing about computers regardless of your technical level. To be fair this is the same of all customer support systems so it’s not an apple specific thing.
I started with the online chat, where I explained the problem and the person on the other end talked me through the obvious steps that I had already tried, such as rebooting my router and so on. He was sort of at a loss, so he suggested I reboot into safe mode and see if that solved the problem, and then contact them again if it was still occurring. If it didn’t occur in safe mode he suggested that I reinstall my operating system. This isn’t exactly a pain free step and to me this was a last resort but anyway. As it was happening to two different computers, I figured I would try booting into safe mode on my MacBook Pro and see what happened, while I tried to continue to troubleshoot on my Mac Studio.
The problem is that the period between when I rebooted and when the issue occurs is completely random and can take several hours so it was going to be a long process. Either way it had to be done, if only to get to the next level of Apple Care.
So I rebooted my MacBook into safe mode and waited to see if it would happen again.
It did not. At least not for the 24 hours I had it booted into safe mode.
So, progress maybe?
Troubleshooting in the 21st century
While I was waiting to see if the issue reoccured on my MacBook Pro, I figured why not ask a different guru if they had any idea of a possible solution.
Enter ChatGPT.
I explained the problem in detail and it was surprisingly robust in its response. It suggested a few possible issues and things I could try including some terminal commands to reset the networking, reset the iCloud cache and things like this.
But even more interestingly it gave me some commands to capture the log files which I was then able to upload to ChatGPT and have it analyse them.
It found a few interesting things. Something was certainly causing network issues but only for certain network calls. It suggested that some application might be the culprit which was borne out by the fact that it didn’t seem to be occurring during the time I was in safe boot on the other system. It made me realise something though: up to this point I had thought that maybe it was private relay being enabled and not being able to disable it that was causing the problem. However, it seemed that the issue of being unable to get the private relay status was a symptom rather than the cause. I was still no closer to finding an answer, but my discussions with Dr. GPT were very helpful and armed me for round two with Apple Care.
This was all happening over the weekend by the way, and during this time I also tested my laptop (now back out of safe mode) at a local cafe using their wifi to make sure it wasn’t a problem with my home network - it wasn’t as the issue reoccured on wifi. I also tried using my phone as a hotspot to doubly rule out the ISP.
Art this point I had narrowed the problem down to being something was interfering with network connections, and it primarily seems to be affecting connections to Apple servers, although the images not loading in mail was still a puzzle.
Again with the Apple Care
Once Monday rolled around, and armed with the new information from ChatGPT’s analysis of my system logs, I ventured back into the chamber of secrets.
In other words, I rang AppleCare. (Or rather I had them ring me, after going back through the chat system.)
One of the most frustrating things about dealing with Any company’s customer support system is having to repeat yourself over and over every time you get referred to a new person. I had to keep asking them to read the case notes so I wouldn’t go insane repeating myself. I was first put on to an entry level person who basically went through everything the first person had gone through before the weekend until they decided that they could then hand me over to a senior support person.
The senior support technician I was connected to was very nice and went through a whole bunch of things with me. They wanted to remotely connect to my computer to control it, which apparently AppleCare can do despite not having any specific software installed to do so. Which is a bit scary, but it does ask permission first. This wasn’t working, so instead they took control of my phone and were able to use the camera to see my Mac screen and system settings. After trying a bunch of stuff they came to the conclusion that we needed to try two things: Reinstall the operating system, and turn off all background extensions.
I really didn’t want to have to reinstall the OS on my Mac Studio so I opted to try it on my MacBook Pro while turning off all background extensions on my MacStudio. Incidentally, I hadn’t realised that you can reinstall the operating system without having to wipe everything. I sort of knew in the back of my head you could do it, but I hadn’t realised how simple it was.
Ok, now what?
So reinstalling the operating system on my MacBook Pro seemed to resolve the issue initially, but then so did turning off all the extensions on my MacStudio. Clearly this was some kind of conflict. However after 48 hours the issue reoccured on my MacBook Pro though so it’s not an issue that a reinstall could fix. At least that was ruled out.
I then turned off all the extensions on my laptop and that seemed to solve the problem there too. So, on both computers I started turning the background extensions back on one by one in an attempt to find the culprit. This was a very slow and laborious task as I needed to wait 48 hours between each reboot to make sure it wasn’t recurring.
Eventually after two weeks I had turned everything back on my Laptop and the problem still hasn’t recurred, so now I’m at a total loss. Almost everything is reenabled on my Mac Studio too and it’s also working fine.
Is it possible that it was a server side issue from Apple after all? Is something on their end conflicting with something on my end? No Idea!
I did have one other theory. I couldn’t figure out why images weren’t loading in mail because of this issue, when I noticed that the Apple Intelligence summaries were also not working. In fact if you tried to manually do a summary it would just hang. I wonder if Apple intelligence is trying to do the summary before the images load and because it’s hanging or can’t contact the server, it’s preventing images from loading? Is this the root cause of the issue? I have no idea, but it might have something to do with it. Or it could be also just a symptom of a larger issue.
Either way, for now it seems to be resolved, even though I’m totally stumped as to the cause (and Apple appears to be too!)
Why are you telling us this?
So, what’s the point of me sharing this slightly long-winded story? Well, I wanted to have a record out there incase anyone else had this problem. When I was searching for solutions, I couldn’t find anyone else having a similar issue, so I want to get a detailed description out in the wild. If anyone has any ideas of what might have caused this, please let me know. And if you did experience this or something similar, also please leave a comment as it might help others in the future.
For now, I’m monitoring the situation but so far so good. Hopefully it doesn’t come back as it was really annoying. Intermittent bugs are the worst to try and solve.
Anyway, now that I’ve gotten that off my chest I can get back to work!
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