The purpose of this article is to review the literature and to highlight current practice regarding the management of the chronic pain patient presenting for surgery. It can be difficult to achieve adequate postoperative analgesia in patients who present for surgery with preexisting chronic pain. Such complex pain patients require a care plan that involves preoperative, intraoperative, and postoperative considerations. Preoperatively, it is important to identify these patients’ specific concerns, to address anxiety, to review expectations of care, and to consider premedication. Intraoperatively, it is important to consider local anesthetic regional anesthesia techniques and to supplement as necessary with pharmaceutical agents, e.g., ketamine, dexamethasone, ketorolac, and opioids. Postoperatively, it is important to continue multimodal analgesia techniques. It is vital to maintain a healthy therapeutic alliance with the patient and with allied health professionals. Nonspecific treatment effects can bolster efforts to achieve adequate analgesia. Successful management of the complex pain patient requires knowledge of the art and science of perioperative medicine.