I would guess an open connection somewhere. It could be on the truck but I would suspect the trailer first. Trailer wiring I've seen is usually not as tidy and well supported and fastened as most new truck wiring.
On my '15 Chevy the display says trailer connected and trailer disconnected when you plug and unplug IF the trailer brakes are functional. If they aren't then it doesn't know. If the trailer brake wiring develops a short it gives me the message "Service trailer brakes". Since you don't have that I suspect an open, not a short.