Oromandibular reconstruction is one of the greatest challenges of the head and neck surgeon. The ideal rehabilitation of the mandible and associated soft tissues requires maintaining premorbid occlusion, providing the opportunity for dental restoration, and preventing salivary incontinence. The approach to each patient must be individualized to maximize speech, swallowing, and mastication. Additionally, the surgeon must strive to fulfill these goals while achieving the most pleasing cosmetic result possible. Although some patients may be treated without reconstruction or with a metal plate and soft tissue flap, the majority of patients benefit from bony reconstruction utilizing a free flap. Reconstruction with free flaps results in more primary healing and fewer wound complications. Challenges specific to reconstructing the temporomandibular joint are discussed. We also review the indications for the different rehabilitative options and the merits of the individual flaps.