Pocket milling is a common machining operation used for removing the material inside a closed boundary on the flat surface of a work piece to a fixed depth(Fig. 1). Rectangular and circular forms of pockets are the standard types of pockets found as canned cycles in the programming capabilities of modern CNC systems. Literature related to automatic CNC pocket machining has recently shown an in creased interest from researchers. This interest is mainly focused on pockets with islands in it (material that is not to be removed), on pockets with free-form profiles and a combination of both [2–6]. The case considered here, does not belong to any of the above-mentioned types of pockets. Modern CNC systems handle similar cases either by the technique of parametric programming or by using a CAD/CAM system to generate the necessary tool path. However, both solutions present serious disadvantages, since both use the segmentation technique to generate the required tool path. Thus, they first approximate the geometric form of the boundary