In the United States nearly one in four patients presenting for surgery reports current opioid use. Many of these patients suffer from chronic pain disorders and opioid tolerance or dependence. Opioid tolerance and preexisting chronic pain disorders present unique challenges in regard to postoperative pain management. These patients benefit from providers who are not only familiar with multimodal pain management and skilled in the assessment of acute pain, but also empathetic to their specific struggles. Chronic pain patients often face stigmas surrounding their opioid use, and this may lead to underestimation and undertreatment of their pain. This article aims to review the challenges presented by these complex patients and provide strategies for treating acute postoperative pain in opioid-tolerant patients.