OT – Upgrading From macOS Mojave To Catalina (The Hard Way)

This post is really about the boring stuff I do when I have a day off and isn’t terribly exciting. TL;DR I had some problems upgrading to Catalina, and had to start from scratch.

 

Background

I’ve had an Apple Mac since around 2008. I upgraded from a 24″ iMac to a 27″ iMac and was super impressed with the process of migrating between machines, primarily because of Time Machine’s ability to recover settings, applications, and data in a fairly seamless fashion. I can’t remember what version of macOS I started with (maybe Leopard?), but I’ve moved steadily through the last few versions with a minimal amount of fuss. I was running Mojave on my iMac late last year when I purchased a refurbished 2018 Mac mini. At the time, I decided not to upgrade to Catalina, as I’d had a few issues with my work laptop and didn’t need the aggravation. So I migrated from the iMac to the Mac mini and kept on keeping on with Mojave.

Fast forward to a April this year, and the Mac mini gave up the ghost. With Apple shutting down its stores here in response to COVID-19, it was a 2 week turnaround at the local repair place to get the machine fixed. In the meantime, I was able to use Time Machine to load everything on a 2012 MacBook Pro that was being used sparingly. It was a bit clunky, but had an internal SSD and 16GB of RAM, so it could handle the basics pretty comfortably. When the Mac mini was repaired, I used Time Machine once again to move everything back. It’s important to note that this is everything (settings, applications, and data) that had been accumulated since 2008. So there’s a bit of cruft associated with this build. A bunch of 32-bit applications that I’d lost track of, widgets that were no longer really in use, and so on.

 

The Big Update

I took the day off on Friday last week. I’d been working a lot of hours since COVID-19 restrictions kicked in here, and I’d been filling my commuting time with day job work (sorry blog!). I thought it would be fun to upgrade the Mac mini to Catalina. I felt that things were in a reasonable enough state that I could work with what it had to offer, and I get twitchy when there’s an upgrade notification on the Settings icon. Just sitting there, taunting me.

I downloaded the installer and pressed on. No dice, my system volume wasn’t formatted with APFS. How could this be? Well, even though APFS has been around for a little while now, I’d been moving my installation across various machines. At the time when the APFS conversion was part of the macOS upgrade, I was running an iMac with a spinning disk as the system volume, and so it never prompted to do that upgrade. When I moved to the Mac mini, I didn’t do any macOS upgrade, so I guess it just kept working with the HFS+ volume. It seems a bit weird that Catalina doesn’t offer a workaround for this, but I may just have been looking in the wrong place. Now, there was a lot of chatter in the forums about rebooting into Recovery Mode and converting the drive to an APFS volume. No matter what I tried, I was unable to do this effectively (either using the Recovery Mode console with Mojave or with Catalina booting from USB). I followed articles like this one but just didn’t have the same experience. And when I erased the system drive and attempted to recover from Time Machine backups, it would re-erase the volume as HFS+. So, I don’t know, I guess I’m an idiot. The solution that finally worked for me was to erase the drive, format it as APFS, install Mojave from scratch, and recover from a Time Machine backup. Unfortunately, though, this seemed to only want to transfer around 800KB of settings data. The normal “wait a few hours while we copy your stuff” just didn’t happen. Sod knows why, but what I did know was that I was really wasting my day off with this stuff.

I also ran in to an issue trying to do the installation from USB. You can read about booting from external devices and the T2 security chip here, here, and here. I lost patience with the process and took a different approach.

 

Is That So Bad?

Not really. I have my Photos library and iTunes media on a separate volume. I have one email account that we have used POP with over the years, but I installed Thunderbird, recovered the profile from my Time Machine data, and modified profiles.ini to point to that profile (causing some flashbacks to my early days on a help desk supporting a Netscape user base). The other thing I had to do was recover my Plex database. You can read more on that here. It actually went reasonably well. I’d been storing my iPhone backups on a separate volume too, and had to follow this process to relocate those backup files. Otherwise, Microsoft, to their credit, has made the reinstallation process super simple with Microsoft 365. Once I had most everything setup again, I was able to perform the upgrade to Catalina.

 

Conclusion

If this process sounds like it was a bit of a pain, it was. I don’t know that Apple has necessarily dropped the ball in terms of usability in the last few years, but sometimes it feels like it. I think I just had really high expectations based on some good fortune I’d enjoyed over the past 12 years. I’m not sure what the term is exactly, but it’s possible that because I’ve invested this much money in a product, I’m more forgiving of the issues associated with the product. Apple has done a great job historically of masking the complexity of technology from the end user. Sometimes, though, you’re going to come across odd situations that potentially push you down an odd path. That’s what I tell myself anyway as I rue the time I lost on this upgrade. Was anyone else’s upgrade to Catalina this annoying?