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MacOS Monterey Upgrade on M1

Published by marco on

I upgraded by by-now 5.5-year-old iMac 27" with MacOS Monterey. It went very, very smoothly. For once, it didn’t even offer to have me connect my Apple account before just loading my user. It just upgraded, rebooted, logged back in, and TADA! all set. ๐Ÿ˜€๐Ÿ’ช๐Ÿผ๐ŸŽ‰

My M1 MacBook Pro, on the other hand, was a good deal more annoying about it. As on the iMac, I have two accounts on the MacBook: my standard user and an “Admin” user. Unlike the iMac, the disk is encrypted on the MacBook. Will I get the same smooth experience? ๐Ÿ€๐Ÿคž(You know I didn’t, else you wouldn’t be reading a block post about it.)

Startup Disk not “authorized” ๐Ÿ˜’

I started the upgrade process on the M1 MacBook, but it quickly balked when it asked me to select a disk on which to install. That was odd, because there’s only one disk. When I selected it, the installer showed a tooltip that read, “You must provide authorization for this volume by setting it as your startup disk. You can relaunch the installer after authorization has been provided.”

 Monterey Startup Disk Tooltip

What the hell does that mean? Is this supposed to help non-technical users get going? I would have set up a relative’s laptop exactly the way I’ve set mine up: encrypt the hard drive and do not use an administrator as your main user. What’s the problem?

I figured that this was because I was running as a non-admin user, but was a bit confused because I hadn’t gotten the same message on my iMac. So, I figured it was a combination of encrypted disk and M1 processor and non-admin user. A quick search confirmed that I should log in as the admin user and I would be allowed to upgrade. That’s fine. It beats installing form the recovery console.

Upgrade as Administrator? ๐Ÿคจ

I switched to the admin user, but the system-upgrade panel for that user just showed a “checking for updates” label with a progress spinner for several minutes. It didn’t look like it was going to offer to upgrade they system for me from the user that actually could perform the upgrade. That’s annoying.

Use the Recovery Console! ๐Ÿ˜‘

So I shut down the MacBook and restarted it by pressing and holding the power button. Holding the power button through the startup process rewards you with a notification that the MacBook with boot “with options”. It soon shows a list of options, including “Reinstall MacOS Monterey”. This was not very reassuring because I had not installed MacOS Monterey yet, but I figured that this was just in keeping with the relatively shoddy upgrade experience thus far. At the very worst, I would have to restore from my Time Machine backup after the installer had wiped everything out. Annoying, but not irrecoverable.

I started the upgrade and it soon told me that it would be done in 2h20m. That’s about 3x longer than the iMac, which is 5+ years older. What is going on? After about 15 minutes, the progress dropped precipitously to 53m. At that point, I left it and went for a long walk (several hours).

Log in and โ€ฆ phew! ๐Ÿ˜ฎโ€๐Ÿ’จ

The upgrade was finished by the time I got back. I logged in and it went back to the white-apple-with-progress-bar-on-black-screen phase, and got stuck at about 90% for at least five minutes.

After that, it was logged back in to the desktop, with my user restored. Oddly, it asked me to log into my Apple Account, which I skipped, as usual, because it was going to be logged in anyway, once it had loaded my user and desktop and open windows.