The parking pawl can get damaged or broken if the tow truck has to drag your truck a bit to get it loaded up when not in neutral. Supposedly a jeep owner last year had placed his Jeep in Park and left the vehicle and the jeep rolled off a cliff with a passenger still in.
Yes, Black Bear Pass. Fortunately the passenger (his girlfriend) is recovering as it was a pretty horrific tumble and she is lucky to be alive.
As part of a off-road recovery group and having formal recovery and rigging training, we always try to convey to those we mentor that the parking pawl should never be relied on to secure a vehicle in place. Especially on a slope! Never when using your winch! From the failures we have observed, the pawl is worn or fractured before the actual failure. That is my PSA for the day.
Different transmissions have different configurations and different spacing between the pawl seats so that is why engagement feels different in different vehicles.