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Hi @jesseatbettercnc,

 

Like @seth.madore said, it isn’t possible with the standard toolpath. 
for the back chamfering you could draw some sketch geometry within the Design workspace that describe the toolpath you are after.  
This is the only way to get your chamfer on the backside. 

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Met vriendelijke groet | Kind regards | Mit freundlichem Gruß

Marco Takx
CAM Programmer & CAM Consultant