Obstructive sleep apnea (OSA) is a common chronic disease characterized by repetitive pharyngeal collapse during sleep. OSA is associated with cardiovascular disease and increased mortality, among other issues. Continuous positive airway pressure (CPAP) is considered first line therapy for OSA, but is not always tolerated. Both non-surgical and surgical alternative management strategies are available for the CPAP intolerant patient. This article explores controversies surrounding airway evaluation, definition of successful treatment, and surgical management of the CPAP intolerant patient with moderate to severe OSA. Controversies specific to maxillomandibular advancement (MMA) are also discussed.