Some MacOS updates require the user to log in before completing the installation of the update. This happens even with the vanilla login window.

Do your machines have FileVault enabled?
With FileVault enable it would hit a login screen before the machine continues to boot, which would pause the upgrade process until the machine is unlocked.

Do your machines have FileVault enabled?
With FileVault enable it would hit a login screen before the machine continues to boot, which I guess would pause the upgrade process until the machine is unlocked.

FileVault is not enabled

Take a look here: https://github.com/kennyb-222/NoMADLoAD_AppleStagedUpdates

I packaged the script and deployed it to my devices, then send a command to execute the script. Now when I update a machine the update actually completes, no having to log in and still having ~10minutes remaining to complete the upgrade. 

I take no credit whatsoever for the script, I just found it and am passing it along. 

Had last question. Do you only need to run this once and any future updates work the same way? or you have to run it every time you upgrade? This script worked out great. Thanks so much!

@coldconfession1 In my experience it only needs to be run once. I can confirm on my machine at least that even upgrading from Big Sur to Monterey it held.