Before I do any more potential damage, need direction from group. When installing screw inlays, I followed a video that showed stepped drill diameters and removing top for countersinking screw head.

I have several that do not tighten down and are not flush with fretboard. Do I need to go to a larger diameter screw, add some sawdust or glue to the hole? Any help appreciated

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Short piece of toothpick and a dab of glue also sounds like hole should be just a smidgen deeper. Same with the counter sink.

I do know how to speak English! For the loose fitting holes, use a toothpick and a dab of glue to give the threads some bite. Next time use a lightly smaller bit and go a little deeper.

Hi Brent, the way I would do it is to countersink by hand, let the screw embed itself into the hole then with a sanding block level all the screws at the same time. Come finer with the sanding grit for a better finish. 

Brass screws look great this way. Make sure you line up the slots in the screws uniformally. 

Taff

I can recommend getting a set of oblique hole countersink bits. The look slighty different from other countersink bits and have the almost magical power to self depth limit based on the outer diameter of the bit being smooth and solid. You do need to drill a pilot hole first but. 

The screws will then bottom out at a uniform depth and shouldn't have to be sanded flush.  

https://www.ebay.com.au/sch/i.html?_from=R40&_nkw=oblique+hole+...

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