Continuing the discussion from Parallel toolpath with no tool raising:
It seems that if you’re running a parallel toolpath and presumably if you’re running it on a flat surface, essentially a raster pocket like Vectric does, you can check the “Contact Point Boundary” box in the Geometry tab in the toolpath and that will allow your endmill to go right up to the edge and move over without raising up and resetting.
Please note my experience is with 2lb closed cell PE foam, and I have already done a contour around the inside of my pocket. Your results may vary, but in my case it’s a super forgiving material and I’m not super worried about the cleanliness of the edge on this pocket, as it’s just a registration mark for a wedge to be inserted later.