Originally Posted By: glum
Better yet, don't overtighten it in the first place.
I'm speaking generally. A drain plug probably isn't the best place to experiment, though the plug should be designed to strip before the pan. My neighbour discovered this last month, and he always used a massive 250 ft-lb torque wrench. After I showed him how to clean up the pan threads with a tap, I taught him to use a normal wrench instead, and that his 1/2" drive ratchet is also not appropriate. It's possible the threads were damaged by someone else though. He hasn't done every single oil change on that vehicle, but he had done every one in the last few years.
I don't even own a torque wrench that is appropriate for drain plug bolts. My little one goes up to 250 in-lb, and I use that for spark plugs and highly compressible gaskets such as in valve covers and transmission pans, while my big one is way too big to be used under 50 ft-lb, despite having markings down to 25 ft-lb. I'd rather go by feel on an appropriate sized wrench than trust that big thing down to the bottom of its range while not being able to feel anything due to its length. I would not consider that to be doing the job right. Of course, there must be appropriate torque wrenches available in a 3/8" socket size. I've just never felt any need to seek one out.
Besides, to me, feeling the tightness of the fasteners with your own fingers on a wrench is one of the pleasures of mechanical work!