Bouveret syndrome was first described in 1896 by Dr. Leon Bouveret who published two case reports. It is a variant of gallstone ileus causing gastric outlet obstruction. We describe a case of Bouveret syndrome presenting as upper gastrointestinal bleeding. An 86 year old male presented with intractable nausea, vomiting, and multiple episodes of coffee ground emesis. His medical history was significant for gastrointestinal bleeding secondary to arteriovenous malformations, atrial flutter, and moderate aortic stenosis. On initial evaluation, patient was found to have a hemoglobin of 8.8 gm/dl. Esophagogastroduodenoscopy (EGD) at a referring institution showed blood in the distal esophagus and bilious fluid in the stomach. The procedure was aborted due to arrhythmia. CT scan of abdomen and pelvis with oral contrast showed a 3.4 cm gallstone in the lumen of the proximal duodenum suggesting gallbladder stone eroding into the duodenum, possibly causing partial obstruction. A small amount of air was seen in the lumen of the gallbladder with entry of oral contrast into the gallbladder suggesting fistulous communication with the duodenum. At our institution, multiple attempts were made to remove the stone by Roth basket, cold snare, and mechanical lithotripsy. Portions of the stone fractured off, but it appeared to be adhered to the duodenal wall. Electrohydraulic lithotripsy not performed due to concern of the potential for precipitation of perforation. The patient underwent uneventful exploratory laparotomy with pyloromyotomy, stone extraction, and pyloroplasty. Gallstone ileus is an unusual complication of cholelithiasis, occurring in less than 0.5% of patients with gallstones. Bouveret's syndrome is a rare variant, and is responsible for 1-4% of all cases of mechanical obstruction. Most commonly the gallstone becomes lodged in the duodenum and causes symptoms consistent with gastric outlet obstruction. Presenting symptoms include nausea and vomiting (86%), abdominal pain (71%), hematemesis in 15%, recent weight loss in 14%, and anorexia in 13% of patients. Diagnosis is usually made through endoscopy. Endoscopic extraction, endoscopic laser lithotripsy (ILL), extracorporeal shockwave lithotripsy (ESWL), and intracorporeal electrohydraulic lithotripsy (IEHL) have all been reported as alternatives to surgery for more proximal gallstone obstruction. Surgical management (enterolithotomy) follows if endoscopic treatment is unsuccessful.Figure 1Figure 2Figure 3