A method that is popular among mandolin makers do is to bind the headstock veneer before it is attached to an oversize peghead, and then trim the peghead to the outline of the binding. I like to rout headstock binding rabbets with a laminate trimmer with a base that has a bearing that indexes off the headstock’s edge. Usually there is some chisel work involved with the transition towards the nut... Personally I’m not too fond of the Benedetto style headstock / fingerboard binding look, I like it better when the nut splits the two. Here's one I just did.

<edit> Hey, I just noticed, this is my post #2000 on the OLF; I just made "Brazilian Rosewood"! Wohooo! Only took 4 years or so... Anyways, that means I get to pick one BRW set from either Lance's or Brock's stash, right? RIGHT!
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