I have the same issue. I have not yet found a way to reliably update iPads using casper.

You have to take battery life and connectivity into play when remote updating. I have been able to update 3k+ within a week without issues but I have to make sure they were a powered and connected.

We have the same issue. I have an iPad sitting net to me running 9.3.4. It is on power, fully charged, and online. I can send other commands to it and they'll get run right away. But I've sent multiple commands for it to update the OS to 9.3.5.

The device never updates. Is this an Apple issue or a JSS issue? When I view the device history, I see the commands were sent to the device:

I have even tried with devices in carts and plugged in with all the batteries at 100%. In a cart of 25 I have never seen over half get the update installed.

We was told buy one of the casper support guys that its got something to do with iPads who have already downloaded the update getting stuck. if the command goes through and the iPad downloads an installs correctly the first time then you don't have any issues. but if the command only triggers the download of the update (and fails to install ) then its going to continue to get stuck. we were told that its a known issue that they are working on...

we got this info during phone conversation so i cant link anything for you sorry.

we have the same issue and i was told it is a bug in this version which will be fixed in future versions.

+1 for the bug.

It appears that the JSS can tell an iOS device to download and install the latest version but can't tell an iOS device to just install the latest, already downloaded, version.

FYI, this is apparently fixed in v9.96.

It is listed in the Release Notes Bug Fixes:
http://docs.jamfsoftware.com/9.96/casper-suite/release-notes/Bug_Fixes_and_Enhancements.html

Search that page for "D-009886" to find the description.

I am testing not but haven't seen much success yet.

Apple recently changed the behavior of these over-the-air OS update commands. As @steelopus noted, the release of Casper Suite 9.96 adopts this new behavior to properly handle OS updates regardless of whether the device has already downloaded the OS update or not.

If you continue to experience issues with the OS Update command, please contact JAMF Support so we can investigate the issue further.