Introduction: Abscess formation in the postoperative bariatric patient can be the result of anastomotic leak, a dreaded complication of Roux-en-Y gastric bypass. However, there is little data on bowel obstruction disrupting the anastomotic site resulting in leak and esophageal dysmotility. Case Report: A 50-year-old female status post laparoscopic Roux-en-Y presents with nausea, vomiting, and epigastric pain. Her clinical course was complicated with small-bowel obstruction, esophageal dysmotility, and an anastomotic leak with anaerobic abscess formation. The patient required a second operation to resolve the obstruction and a third operation to drain the resulting abdominal abscess. Conclusion: This case highlights a unique presentation of a post obstructive abscess following Roux-en-Y gastric bypass. A high index of suspicion should be maintained in postoperative bariatric patients presenting with symptoms of dysphagia and bowel obstruction without overt signs of infection to optimize prognosis and quality of care.