This paper presents a computer aided process planning (CAPP) system for numerical control tool path generation of complex shoe molds. This CAPP system includes both the automation of auxiliary boundary curve generation and machining strategies. The automation of auxiliary boundary curve generation and machining strategies make tool path generation more accurately and efficiently. Traditional shoe mold making is a very tedious process. Even with the utilization of computer-aided design and computer-aided manufacturing (CAD/CAM), the CAM process requires long hours of tool path programming and debugging. It would also take a long time to calculate (sometimes several hours) the tool path for complex athletic footwear. In order to reduce the tool path editing and programming time, this paper proposes the use of CAPP to reduce processing time and increase efficiency. It is difficult, if not impossible, to develop a generic CAPP system that can generate a process plan to solve general production problems. However, it is quite possible to capture the domain knowledge of a certain production process and embed that knowledge into a CAPP system. We prove, by using such a system, that a very complicated process planning problem can be overcome by a knowledge-based CAPP approach. With such an approach, the traditional manufacturing process of shoe molds can be converted to an automatic manufacturing process with the CAPP system. In fact, shoe molds for real production have been created using the developed CAPP system, demonstrating the effectiveness of this approach. In this paper, we show that several complex and different shoe molds and their machining strategies were automatically planned by the proposed CAPP system. The result of a comparison between the CAPP system with the traditional approach is presented and discussed.