Workflow for updating Mac OS from Catalina to Monterrey (Intel & M1)

@nick_presko erase-install: https://github.com/grahampugh/erase-install Ignore the name, it also does updates. See the Jamf Pro section of the Wiki for instructions: https://github.com/grahampugh/erase-install/wiki/8.-Use-in-Jamf-Pro

I'd strongly recommend using the --depnotify option as that will give your users a much better idea of the update progress.

we are also using erase-install for the upgrade. Works like a charm. 

Second (third?) the recommendation for Erase-Install. We used it to upgrade our fleet, most of which were on Catalina. 

Thanks for all the great info! I have started using erase-install and have had some success with Catalina to Monterrey. But now going from Big Sur to Monterrey I get this message and can't find any info on it. Anybody have an idea what to do?

As far as I know, you receive this pop-up with Apple arm64 processor, as Apple arm64 requires this user authentication. You can reduce this popup bei adding the -user or --current-user parameter in your command.

As @MehdiYawari mentions, this is a requirement on Macs with Apple Silicon processors. Unfortunately editing the erase-install script as the mentions isn't practical unless every Mac you'll be running the script on has the same volume owner account with the same password and you're ok modifying the script to inject the password (you really shouldn't). Also don't run erase-install without a logged in user as it will automatically try and use the logged in user to authenticate the upgrade (it will still require entering their password). For those Macs if responding to that prompt is truly a problem you might try using Jamf Pro to send a management command to force an update to macOS Monterey as that path doesn't require user interaction. Unfortunately "reliable" is not a word one can use to describe the MDM initiated update process for macOS.