Discontent

Famously, Macs Just Work™ up until the point they don’t. We have an old (2014) Mac mini connected to the TV to act as a more capable media player and server than an Apple TV would be. Previously, after Apple chose not to fix the webp exploit on its last officially supported OS (Catalina), I used OpenCore Legacy Patcher to standardize on Ventura on every Mac in the house that still gets turned on. This was fine as it goes, and I’m able to install updates without any issues on a similarly unsupported MacBook Pro from 2015.

This week, however, the Mac mini stopped updating. The installer for the latest Safari update crashed without successful completion, and Ventura 13.6.1 wasn’t showing up in Software Update at all. Delving into the Console app I found the root error was the shove process crashing with a doesNotRecognizeSelector error message. I exhausted the amount of time I was willing to spend on it, and that should have been that.

But then my wife asked for her annual supply of Christmas music from my CD collection, which for disk space reasons is only in my Music-formerly-iTunes library and not hers. (There does not seem to be a good way to share a music library across users, or at least there wasn't the last time I looked for one). Putting my music on her iPhone requires plugging her iPhone into the computer where the library lives and syncing manually. It's a pain, but most of the time this doesn't matter, because we can fill it up with the stuff she likes and forget about it. Unfortunately, the computer where the library lives happens to be the Mac mini that previously failed at Software Update.

That same Mac mini, unsurprisingly, required the installation of some software component so it could connect to her iPhone, and when I tried to install it the same shove process crashed with the same sort of doesNotRecognizeSelector error message.

Good news, everyone! This is not a problem Apple will help you fix. Leaving aside the not-inconsequential issue that Ventura isn't officially supported on this Mac, their guidance for problems like this is just to reinstall the OS and restore from a backup. I went back to the thumb drive I'd used for the installer, but the installer said that the volume couldn't be downgraded. Um, what?

So then I downloaded the full 13.6.1 installer and used the media creation tool to put that on my thumb drive instead of whatever older version of Ventura was on there. 13.6.1 is newer than the 13.6 that was installed on the Mac, so that installation should work, right? Wrong. Even the 13.6.1 installer said that the volume couldn't be downgraded.

At this point I followed the usual guidance and created a new volume on the startup drive, but then the installer said there wasn't enough room on the volume. After I deleted 4 GB of old media files to clear up the 1.5 GB I needed, the installer still said there wasn't enough room on the volume. Frustrated, I wiped out the Time Machine snapshots on the original volume and that made enough room for installation.

After letting the installer do its thing, I tried to use Migration Assistant to copy everything from the old startup volume to the new one, but here's where this gets really weird: Migration Assistant refused to allow me to select the old startup volume, saying it that it was a newer version of the OS and that the current startup volume would need to be upgraded first.

Based on that I'm pretty certain that some indicator of the current installed OS version on the old startup volume has gotten corrupted. But because this is not a problem Apple will in any way help you resolve, what I'm left with is a tedious, manual process to look over the old startup volume and its user directories, find the things that should be copied, and copy them with the correct permissions into the corresponding places on the new startup volume. Several hours of work across three days later, I've got most of the important stuff done but I still have some lingering issues.

I thought I had gotten the Music library all set up again, but then it turned out that merely pointing the app at the directory containing all its media wasn't enough. I had to import all the files that were already in the media directory (almost a thousand albums, more than 12,000 songs, which could play nonstop, without repeat, for 31 days). And of course since it's a new installation my wife's iPhone doesn't recognize it as the library that was previously synced. Doesn't matter that it's the same hardware, the same library files copied into the active user's home directory, and the same media folder on the same hard drive. Now, just to get Christmas music onto her iPhone, I've had to take notes (by hand) of what music was already on her phone, set up the sync with the new copy of the same library, and then restore all the old music when adding Christmas music.

Even weirder, there's a handful of playlists that are either empty now or just don't show up in the interface where you select which music to sync. The music exists in the library, but the playlists can't be selected. I think this is caused by a workaround I previously had to put in place for stuff that iTunes Match mismatched (e.g. mono tracks from remastered Beatles albums that iTunes Match replaced with the stereo versions), but I have to stop somewhere. That can be a problem for another day.

Ironically, the non-Apple media server software I use for TV and movies (Emby) worked perfectly once I copied the old configuration directory over, recognizing all the local media directories I'd previously configured. It's just the Apple software that didn't work right the first time. There's probably a lesson in there somewhere.