I have been reading (all right, skimming) every source I can lay my hands on, and the following possibilities present themselves:

1. In < href="http://www.mudcat.org/thread.cfm?threadid=62576&messages=87#1012367">Gareth's post above re. Horblower's capture of the "Estrella del Sur". Apparently, the swimmers detailed for the job of knobbling the "Estrella" used knives to pry the copper off one of the rudder braces below the waterline, then used an auger to drill a hole large enough to pass a stout line through, to which the drogue was attached. Since this was underneath the ship's counter, I suppose it possible that they could find rudder pintles and other projections from the ship's hull to brace themselves against while they pried and drilled.

2. In the case of the "Golden Vanity", we may all have overlooked one possibility; that the Spanish or whatever enemy vessel sunk by the cabin boy was grounded at low tide (happens a lot in the Low Countries). This would explain why her crew had leisure to play snap, or snakes and ladders, or whatever. The cabin boy could stand on a solid bottom and work against a similarly immovable ship's hull. After a few hours, the tide comes in, glug, glug, glub, bubble.

3. The ship's crew in life belts ? When were these introduced ? It could give us a "not-before" date for this song, unless the dreaded "folk process" added this little touch over the course of time.