It is not so much "will" you hit the cab, it is "when will" you hit the cab. Chris
Last fall when I was at the Chevy dealership where I bought my truck getting an oil change before our pull to the Las Vegas Rally there was a 2015 or 2016 Chevy 2500HD short box in front of me while we were both signing in.
His back window was smashed out, along with some cab damage.
I overheard him telling the service guy that he did that with his 5th-wheel trailer.
I didn't get a chance to talk with the guy or take a closer look at his truck before it was whisked away to the body shop and he had a ride to take him home.
He had a tonneau cover over the bed so I didn't get a look at his hitch, either.