We go over a bit on dovetail tooling at:
On a CNC it’s best to use a square tool to remove the bulk of the material — the difficulty is setting up a toolpath where the tool plunges at the correct place, stays at the correct depth for the entire cut, then comes out and only lifts where it is safe to. Unfortunately, Carbide Create can’t model undercuts, so one has to take this on a bit of faith.