If you are talking about being unlevel side-to-side, you put lego blocks under the trailer tires and now the trailer is (approximately) level side-to-side and the truck is still on a side-to-side slope, yes ... if the slope (side-to-side) is steep enough, it can prevent the jaws from releasing.
What you need to do is block the tires under the truck as well so both truck and trailer are level side to side. When you hitch back up, you'll need to place those same blocks under the truck tires again, so truck and trailer stay (somewhat) level side-to-side.
It takes some practice to do this. But get the trailer in a level position first with the lego block or boards under the tires. Then pull forward just enough to put the equivalent "lift" under the tires of the truck, and then back up onto those block or boards. Truck and trailer and now more level, side-to-side, with each other.
This is the only way I know how to do it and I've done it this way myself. It ain't easy, but it does work.
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2019 Montana High Country 375FL
2014 Chevy Duramax HD 6.6 - 3500 Diesel Dully Long bed Crew Cab
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