Don't take my advice as I am no expert. Look at the peg head angle. File at that angle. This will make the highest point on the fret board side. File once, one swipe, and reevaluate. It may file down super fast. At least in my experience it did. The break point is an edge not a ledge. Good luck.
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Waterloo WL-S, K & K mini
Waterloo WL-S Deluxe, K & K mini
Iris OG, 12 fret, slot head, K & K mini
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