For general communication, the APNs is the only thing that matters. First thing to confirm is can you push an Update Inventory to the device? When was the last time it reported its inventory? Is the APNs expired? If it was renewed recently we can check what topic is reported in Jamf Pro and then go onto he devices in Settings and look at the MDM profile there to confirm that the topics match (if a different certificate was uploaded to Jamf Pro this would cause the devices to not communicate anymore)
Once confirming general communication, is this the only device not receiving the application? Is it just the application or are other things stuck in pending? The VPP Token would be tied only to app deployment so if that's the issue I would assume config profiles and inventory updates would succeed.
Just wanting to confirm in the management command section of the device it does just say 'Pending' not that it failed or some other error.
Outside of that, just to confirm general network connection that we aren't on a network with a firewall or anything that could hinder the devices from reaching the Jamf Cloud server.
