I'm finding that now having a case on the iPad and not being plugged into power when the download completes is interrupting the process. We use stm DUX cases on our iPads, and upon testing I could not get it to go if the lid of the case was closed. And, even if the battery percentage is above 50%, the update still won't work...

We ask that everyone plug them in - having the case open with the magnetic sleep type cases definitely seems to help - I have found that sending remove passcode prior to sending Update iOS helped in the past as well (I only do it on iPads with no passcode so I don't know why it helped but it did) Last time I tested it iPads with a passcode wouldn't update until they got unlocked but removing the passcode obviously isn't a realistic workaround for that.

I am finding that overall it works roughly 10% of the time. Occasionally we will have a failure that we can clear and retry but nearly always it gets stuck and just resends OSUpdateStatus over and over again until we manually update the iPads. The feature is basically useless.

Useless may be too harsh, checking the status of the iOS updates that fail 90% of the time helps me to find the individual app updates that are reinstalling every 5 minutes in infinite loops on every iPad they are scoped to because updating apps is too much of a challenge for Jamf too.

I have noticed that if there are any pending or failed commands, then the iPads just won't perform the update. They receive the message but nothing happens. I have also noticed that even when the update is complete, inventory doesn't update the version number until you get past the update screen. "Update completed. Blah blah blah." and press continue. Once you are back on the Home Screen, it seems to report the new iOS version in inventory.