Reconstruction of the ascending portion of the mandible, including the angle, ramus, and condyle, can be a challenging surgical problem. Many treatment options are available, but no single procedure has been able to restore long-term form and function in every case. Currently, autologous nonvascularized bone grafts are the most common treatment, with the costochondral graft as the historic leader. Nonvascularized grafts can often restore vertical height and normal function but may face the challenge of long-term durability secondary to bone resorption. Emerging techniques in microvascular surgery may offer an alternative approach with the benefits of resistance to resorption and infection by maintaining a viable blood supply to the graft. Vascularized grafts may thus be used to full advantage in cases where prior surgery, scarring, disrupted vasculature, or radiation damage may compromise the long-term surgical success of a nonvascularized graft. This article reviews the literature and summarizes key points regarding nonvascularized and vascularized treatment modalities for reconstruction of the ascending mandible. In addition, we present the use of the femoral medial epicondyle free flap based on the descending genicular vascular pedicle as a novel reconstruction of the ascending portion of the mandible with minimal donor-site morbidity. Knowledge of all available options will aid the surgeon in achieving the optimal reconstruction for their patient and improve long-term outcomes.