In recent years, bimaxillary rotation advancement (BRA) has become the method of choice for surgical treatment of obstructive sleep apnea (OSA). As dislocation of the jaw bones affects both, airways and facial contours, surgeons are facing the challenge of finding an optimal jaw position that allows for the reestablishment of normal airway ventilation and esthetic surgical outcome. Owing to the complexity of the facial anatomy and its mechanical behavior, individual planning of surgical OSA treatment under consideration of functional and esthetic aspects presents a challenge that surgeons typically approach in a non-quantitative manner using subjective evaluation and clinical experience. This paper describes a framework for individual planning of OSA treatment using bimaxillary rotation advancement, which relies on computational modeling of hard and soft tissue mechanics. The described framework for simulation of functional and esthetic post-surgery outcome was used in 10 OSA patients. Comparison of the simulation results with post-surgery data reveals that biomechanical simulation provides a reliable estimate for post-surgery facial tissue behavior and antero-posterior airway extension, but fails to accurately describe a surprisingly large lateral stretch of the velopharyngeal region. This discrepancy is traced back to anisotropic effects of pharyngeal muscles. Possible approaches to improving the accuracy of model predictions and defining sharp criteria for optimizing combined OSA planning are discussed.