Another good question,
I have seen a trailer where the jockey wheel did "work loose" and fall to the ground whilst towing. The tyre was obliterated, the wheel hub badly bent, and the actual jockey wheel stem was bent.
The driver told me he became aware of a bump , followed by quite a vibration, then a grinding noise, all the matter of about 100 meters. :huh:
On inspection the jaw clamp that held the jockey wheel stem was not fully closed and tightened up. The owner went on to tell me the clamping handle had been stiff for some time, so I guess he simply hadn't fully clamped the jockey wheel.
I have also seen a number of caravans where the jockey wheel jack screw was quite free when it was unloaded, and unless it was fully screwed up and firmly against its end stop, it might have started to work down with the motion and vibration of towing.
As you say prevention is much better than cure. The first thing is maintenance, make sure the locking clamp thread is greased and easy running and pulls up tight. :evil: The obvious thing is to double check the locking of the jockey wheel when you hitch up, and the prevention I have used, and continue to use does two jobs, I use a piece of bungee chord or rubber band made from an old inner tube around the jockey wheel handle and use the other end to lift the 12V electric cables, so there is no chance of them dragging on the floor when towing. It can also be useful to keep the plugs off the ground in storage.