Thanks so much for the response. I’m actually not pocketing the smaller geometry, but leaving them untouched - think of creating a rubber stamp. So I want to carve out the exterior, everything around the shapes, using a bigger bit for faster removal, then come in with an 1/8" bit to get between the shapes, but leaving them at their original surface level. So when I deselect the smaller geometry, it says it will just pocket the whole thing. I’ve attached a simpler file - it only works when I keep the ovals selected. This one doesn’t hang because the bit size fits, but hopefully it makes sense…I’m fine to do the manual rest machining, but just not clear how to define the pocket area properly. Sample.c2d (37.1 KB)