This just started happening a couple weeks ago and I cannot find a solution.

Lately when my iPhone XS is connected to USB audio, it randomly just stops playing the music. The files are on the phone, not streaming form the cloud. Same thing happens if I choose bluetooth but have the phone still plugged in to USB to charge. But works fine if not plugged in over bluetooth.

Anyone else deal with this issue? The head has the latest software, and no phone updates have been made. Worked as it should for the last year and a half.

Is it possible to reinstall the software if already up to date? I have deleted and re-paired the phone, cleared all user data from the headhunt back to factory, and restored the phone. Still happening, some days it works for a while, and some days not at all.

I know Entune sucks, as much as I would like to, just not in a place to replace the head unit right now.

entune indeed sucks.

What I am assuming is the entune system does not want to pay whatever fee, if any, to apple to support the function of playing music via usb cable.

when you're plugged in via usb, check to make sure your bluetooth is connected in entune. I know sometimes when i plug in my bluetooth on entune is cut off and it needs to reconnect.
i think you have to press the source button and/or device button in entune.

try that out. or try reseting your phone.