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You were giving it to many inputs. Sometimes (often) in 3D, less is better.

Using the 3D contour you had, I changed some of the selections around. I think you will find the toolpath was what you were looking for. That being said, I'd prefer the Ramping toolpath myself, as it will be a better finish, maintain constant contact so on and so forth

 

Countersink 3D1.PNG

 

If you replicate all the choices you see in the image above, you will get the path you want. Note: One profile selected, Tool center on boundary. You actualy don't need the Avoid/Touch option, I just forgot to turn it off. Tried it out and it is not needed..

On the Bottom Height, remove your negative offset. Simply select that bottom edge


Seth Madore
Owner, Liberty Machine, Inc.
Good. Fast. Cheap. Pick two.