Technology for milling selected portions of a workpiece by a cutting tool of a numerical control machine is described. The described technology can receive a main toolpath, the main toolpath comprising one or more cuts; compute one or more transition toolpaths, each transition toolpath defining a transition area intersecting one or more of the cuts of the main toolpath; trim one or more cuts of the main toolpath near two or more points of intersection between the main toolpath and the transition toolpaths; connect the trimmed portions of the main toolpath with one or more connecting moves such that each connecting move is mostly inside one or more of the transition areas; and mill the selected portions of the workpiece by moving the cutting tool in accordance with the cuts, transition toolpaths, trimmed cuts, and connecting moves.