Initially we had a policy that set restrictions, OTA enrollment, and established self-service. However, we were laying hands on each device to enter wifi passwords, so we created another policy that populated wifi info and made the link for OTA enrollment, and deployed this through Configurator. We then had students do OTA enrollment to set the remaining restrictions and self-service with a policy distributed by Casper. This seemed to work fine for a time, but lately we have been seeing devices which accept the first policy, giving wifi and the OTA link, but then eliminate the second policy, even after enrollment seems to confirm acceptance of the second policy. When checking profiles you can see all of them listed, and then right before your eyes you see the secondary policy disappear, and only the original policy remain, and the self service icon disappears as well as any restrictions that had been established by the secondary policy.
Between updates to iOS and Casper it is hard to determine where things might have broken. Anyone else experiencing similar issues, or have an idea where the conflict might lie?
Let's start with the basics..
Hopefully you have updated Configurator to 1.4.
Are your devices still supervised? Settings -> General -> About should say "This iPad is supervised by ....."
Is this happening when you plug the device back into Configurator? Make sure the preference for 'When a supervised device is refreshed' is not set to 'Remove apps and profiles Configurator did not install'. I also turn off 'Automatically Refresh'. (I restore a backup with Configurator when first Preparing an iPad, and then go to the Supervision screen and change from that backup name to 'Don't restore backup' to make sure I don't fully reset the device.)