A fifth wheel uses a mechanical lock, and any mechanical device can fail. However, the chances of it happening are highly unlikely. To be able to release the locking latch on a fifth wheel, the pressure must first be taken off of the locking latches. When the trailer is being pulled, the pressure on these prevents them from coming undone. In the James Bond movie, Licence to Kill, James Bond is shown releasing a tractor from its trailer and letting it roll down a cliff to take out a fleet of vehicles - in reality, he would've never been able to uncouple that truck from that trailer.
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