I work for an MSP and one of our clients is a school with around 150+ iPads over multiple campuses.
We've recently made the move from Meraki to jamf and with 115 of them sitting in various states of OS versions, I don't seem to be able to get them past the update scheduled stage without getting hands-on with it and manually installing it.
They're set to allow automatic checking for updates and scheduled times are outside of school hours. Pushing the install doesn't seem to override this and in a lot of instances, the OS doesn't seem to autonomously update as expected during the set time frame.