Being in the Coast Guard, I hear of some interesting stories.
One of the best I've heard read was in Boating magazine a few years ago.
A captain was taking out his yacht alone and towing the dingy. As he was headed out to sea, he noticed the dingy had water in it and was swaying pretty bad since the water was collected in the forward part of the dingy in the deep v portion.
The captain decided to set the autopilot to avoid losing time, went to the swim platform and pulled the dingy up and jumped in to bail it out. The dingy began to sway worse so he moved to the stern. The boat settled down and he bailed it out.
However, when he went forward to pull himself back to his yacht, the dingy began to sway dangerously out of control so he crawled to to stern to settle it down again. This happened several times. With the autopilot on, the boat continued on its way out to sea.
After a considerable amount of time, the situation was getting very serious. The sun was going down and the captain was scared the situation was going to continue until the yacht ran out of fuel which was about 1400 miles from his origination.
Finally he managed to lay in the bottom of the boat and pull himself to the platform and get safely out of the dingy... ... ... ... lesson learned.