Dont have a drill press, just hand held. Most Tuner holes require a two sized hole for grommet.

what us the secret in not  gouging hole lip when starting the larger hole over smaller?

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Drill the larger hole 1st is one way around that

Exactly, drilling the smaller hole first is a rookie mistake in woodworking.  We've probably all done it at some point; I know I have.

Hi, what ever method you use, I'd suggest a bradpoint drill bit. Start with a 1/16 drill right through, then come in from both sides of the  peghead with the appropriate size bradpoint drill bit. Thats what I do anyway.

Taff

Yup, brad points are the way to go for tuner holes. Another tip to stop tearing is to start your holes in reverse until you are through the surface of the wood.

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