Systems, methods, software and techniques for generating a milling path for a tool of a surgical system are provided. The milling path is designed to remove a resection volume associated with an anatomical volume. A reference guide is defined with respect to the resection volume. Sections are defined along the reference guide in succession. Each section intersects the reference guide at a different intersection point and is at a specified orientation relative to the reference guide at the intersection point. Each section further intersects the resection volume. A section path is generated to be bounded within each section and defined relative to the resection volume. A plurality of transition segments are generated and each transition segment connects section paths of successive sections along the reference guide.
