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I apologize if this is not in the right place, I tried searching for my question but didn't come up with much. Thanks!

I'm working on some Oak furniture, with #8 wood screws.

I have a #8 countersink, as well as a #10 countersink. (Counterbores? Countersink+bit for pilot hole).
I have just purchased 1/4in and 3/8in Plug Cutters, and neither are filling my need.

My #8 countersink for some reason has two tiers (? and 3/8), but I can't get deep enough in this wood (Thin) to get to the 3/8 "shoulder" on this bit, it's just drilling a nice deep hole on the smaller "tier" of the bit. A 1/4in plug is too small to fill this hole, and 3/8 too big!

My #10 countersink makes a perfect 3/8 hole, but I'm worried about putting #8 screws in a #10 pilot hole, even though the seem like they're quite snug to me.

At the moment I'm considering using the #10 bit to drill all my pilots, even though I've got #8 screws… Or, I could put the #8 drill bit inside the #10 countersink, but that seems like it might be a really bad idea and introduce a lot of wobble or weirdness….
 
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