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I'll second the Forster bits. They are so much easier to work with as well. Be good to cover what every your drilling with masking tape. This helps. But wont prevent all the chipping.
I used to drill a 1" hole all the way thru then glue on a piece of 1/8 or 1/4" plywood on the inside of the box with the 3/8" hole in it. I felt that the plywood was stronger than most of the soft woods that the boxes were made of. Probably over kill, but what the heck.
Another thing is - next time you buy jacks - go for ones with a long thread. Most are made to just pass through a thin jack plate, but the ones I buy can easily get through a 8-9mm box side.
+1 on the jack plate, whether it's a metal one or a piece of wood - I wouldn't use a paddle bit on any part of a guitar. Too messy :)
be careful how you drill a hole this wide into a cigar box, paddle drills and Forster bits are designed to cut through solid wood not cigar boxes - safest way is drill a small pilot hole and cut the larger hole with a jig saw or fret saw, or use a circular drill bit or hole cutter, clamp a block of wood to the inner side of the lid or cigar box wall while drilling...
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