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Dave,

Are you milling that in a drill press? (from the pic it looks like a similar model to what I have)

If so, how you keep the vibrations from loosening the taper and dropping the chuck?

I tried to do some basic milling of aluminum with my drill press with a pretty small end mill and I could't keep the taper from letting go and dropping the whole chuck onto the workpiece (and then onto the floor).? I finally gave up.