Watched a video by a pro builder pressing grommets into a headstock using a purpose built press. I was fiddling with a few things to see if I could replicate something similar with stuff I had in my shed when I noticed my many Phillips head screwdrivers seem built for the job. Slip the grommet on the screwdriver. Push it in and a couple of taps with the hammer and Robbert is your avuncular relation! 

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Nice!  I just use one of those squeezable hand clamps myself.  Seems to do the job.  Your idea will ensure it'll go in straight!

Awesome! I also use a spring loaded center punch to install 1/8" brass eyelets for string ferrules...

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