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Jeff, picture a marshmallow skewered on a stick, with the stick tip exposed.

Do you stick the ear plug on the bit, then it adjusts itself as you drill, advancing itself?

foam ear plug?

What do you have. A 1/4" by 12" or so would work. Drill into the roots, too. Try not to drill through and "dirt" the drill tip. Call local tree services for a drop-and-leave quote. Maybe check with Nick (screen name Bonner1040, I think) at TreeStuff for a drop and leave price. Can't be...