Well I have joined the club. Pulled out yesterday and while straightening out the trailer became detached. the box on the old truck is wasted. I was wondering what kind of damage others have seen on ...
OP sounds like the typical high pin or high hitched. A high pin or high hitched is when the pin is too high and the bottom of the pin (flange) slides across the top of the jaws just enough to close them with the usual bang.
High pin/high hitched will sometime pass the pull test as there may be 2000-4000 lb sitting on the jaws and come off the first corner or at some point down the road. Thats why its important to do a visual after you hook up.