Basically what I am trying to figure out how to do is if you were to run an end mill thru a cylinder perpendicular to its axis and then rotate the mill side to side 23 degrees each way like shown in the pic below. Can anyone figure out an easy way to do this? My brain is just not working on all cylinders today.

Thanks in advance,

Chris

I used this sketch on a plane perpendicular to the cylinder to make an extrude cut to the diameter of the cutter

then added fillets

and I don't know what you need for draft - currently there are faces with down to 0 degrees, but that meets the 8 degree max