Mandibular reconstruction is typically performed for traumatic or postsurgical conditions, and may involve the use of autologous osteocutaneous fibula free flaps for large defects. Recreating the native contour of the mandible during reconstructive surgery is challenging. Existed pre-operative planning software has limitations. In this paper we present a novel pre-operative planning system that helps to optimize the number and location of bony osteotomies, and the orientation of the harvested bone segments by specifically prioritizing the position and number of the cutanteous perforators to the osteocutaneous fibula free flap, in order to improve the reliability of the osteocutaneous fibula free flap.