Well, they had me wait an hour and a half to no avail.
The Tech said every time he attempted to do the update it would kick out, so they gave me a loaner car...2019 Camaro RS with 534 miles, which was a nice bonus and told me to come back possibly tomorrow. I got in the loaner, plugged in my iPhone and it worked perfectly in there, so that seems to rule out my phone or cords as the issue