With the dramatic increase in obesity surgery and the subsequent increase in ageing post-gastric bypass patients, early recognition of possible and serious complications is of the utmost importance. We present a case of a 33-year-old woman who presented to the emergency room, with progressive epigastric pain. The patient had undergone laparoscopic Roux-en-Y gastric bypass surgery 14 months earlier. Diagnostic laparoscopy was performed and showed a prepyloric perforation of the gastric remnant. The defect was closed and omentoplasty was performed. The patient was put on lifelong proton pump inhibitors.