Monterey to Sonoma Update Speed Bumps? (or even from Catalina!?!)

I am a VERY slow updater for macOS. It always starts out as “let other people discover the bugs first.” Then, inertia and laziness set in.

This means my work machine (14" M1 MBP) is on Monterey, and my home iMac (a 2020 27" Intel) is on Catalina (10.15).

I’ve decided that this spring is the time to get my OS house in order. Are there any horror stories I should be aware of in updating over multiple versions at once? I have 2 non-bootable clone backups in rotation for both machines (as well as Backblaze, and Time Machine for my work but not home machine), and will make sure both are very recent before updating.

Anything specific I should be worried about?

Seeing how far behind I’ve gotten, I think I may go into automatic updating, since the last couple of major OS releases seem to have been pretty stable. If the beta reports sound rocky, I can turn off auto updating…

Thanks!

-Eric

I recently upgraded an iMac Pro from Mojave to Sonoma. The only scare was that the screen was black after the first boot into Sonoma. I could see dialog boxes but not windows. I poked at things for a while and eventually got to a visible desktop, but I’m still not sure what was wrong. I’ve seen other reports of this issue with the same eventual resolution but not a solid explanation.

I updated third party software where I could before I did the upgrade, but there were still actively developed apps I depend on that wouldn’t run after the upgrade. Expect to spend some time finding/installing updated versions, although it likely won’t be nearly as bad since you’re past the big Mojave → Catalina transition.

The only thing that’s still an issue for me is that Time Machine is very, very, very slow to a NAS now. It’s hundreds of times slower than using Carbon Copy Cloner to a directly attached SSD and so basically unusable. I’ve seen many reports of this problem but it’s not universal. I have newer NAS hardware that I’ve been meaning to try but haven’t gotten to it yet.