Psychosocial evaluations are a standard part of the multidisciplinary assessment for patients seeking bariatric surgery. Fewer than 5% of patients are deemed to be inappropriate for surgery by a behavioral health (BH) provider. When conducting initial evaluations, BH providers do tend to uncover interesting and often complex factors that may put patients at risk for poor results or further medical and psychiatric problems after surgery. With the goal of 'getting patients to surgery', these factors may slow down the patient's process. The BH providers are then tasked with improving readiness and knowledge, but psychoeducation and cognitive behavioral treatments may not be effective for all patients. The following panel includes three cases presentations of patients who had multiple challenges beyond disordered eating. We will review initial impressions from the evaluation, recommendations, and subsequent treatment, challenges, and progress. We aim to provide our insight into complex medical and psychological issues with these patients, and have a discussion with our audience to exchange ideas, information, and experience.