The postoperative management of advanced resectable head and neck cancer has evolved substantially in recent years. A better understanding of the risk associated with specific tumor- and treatment-related factors now allows physicians to predict outcome more accurately, to counsel their patients more appropriately, and to individualize treatments more precisely than ever before. The importance of the amount of time that elapses from the date of surgery to the date radiation therapy begins (and to the date it ends) has been examined, and strategies to counteract the deleterious repopulation of tumor cells during prolonged intervals have been devised. The potential benefit of concurrent postoperative cisplatin chemotherapy and radiotherapy in high-risk patients has been demonstrated in several small trials and two large prospective randomized trials. Used in combination with postoperative radiation therapy, trials of other cytotoxic drugs and targeted therapies are being planned, and some are already being tested. The future will likely demand more complex treatment schemes from physicians but holds a greater prospect of success for patients.