In the postoperative pain setting, the use of opioid analgesics remains essential in achieving effective analgesia and in avoiding the deleterious sequelae of uncontrolled pain that can worsen patient outcomes. However, postoperative pain remains undertreated in many patients. Choosing the most appropriate use of opioids in the postoperative setting, especially for patients undergoing ongoing opioid treatment for chronic pain, can pose daunting challenges for many clinicians. In this article, we examine the pitfalls that may be encountered when implementing postoperative pain management strategies with opioid analgesics, especially in patients receiving chronic opioid therapy prior to admission, and the critical steps for appropriate and effective analgesia in this setting.