Hey There, Connor here from Meraki Support.
If the iPad is supervised, you may be disabled Pairing. The iPad will "show up" on a connected PC, but you won't be able to transfer files and the iPad won't prompt. Under System Manager > Devices > * select device*, on the device page you should see "Supervised: True or false", if it's true, it's likely that pairing was disabled.
Kind regards,
--
Connor Loughlin
Network Support Engineer
.:|:.:|:. Cisco Meraki EMEAR
🇬🇧For reference, many questions can be easily answered by searching our online documentation:
http://documentation.meraki.com