Another winch question

[AJ Oliver]

Just bought an expensive Milwaukee 1/2" D-Handle Right Angle Drill
to raise the daggerboard (at the dock only of course)

The problem is that my starboard cabin top winch is self-tailing, and works
counter-clockwise only. When powered, the chock of the drill just spins right off.

Suggestions ?

[Jameso]

My guess is a broken pawl or pawl spring for the second gear assembly. You’ll need to take the winch apart to confirm, the pawls for the low gear are housed in the gear set beneath the main spindle. There is a chrome push pin holding it in place. Good luck.

[Pete]

I assume you've tried operating the winch in both directions with the handle to confirm it's OK. Could be that your powered tool can operate in one direction only ?