Bouveret’s Syndrome is the rarest form of gallstone ileus. It is characterized by the passage of a large gallstone through a cholecystoduodenal fistula resulting in obstruction of the proximal bowel. The rarity, and non-specific presentation of Bouveret’s Syndrome, make it a frequently overlooked diagnosis, with a significant associated mortality. We report the case of an 86 year old male presenting to the Emergency Department with nausea, vomiting, and constipation. Diagnosis of Bouveret’s Syndrome was made by CT scan of the abdomen demonstrating a large stone in the proximal duodenum. After failed attempts at endoscopic removal of the gallstone, the patient was taken for surgical enterotomy and foreign body retrieval. Bouveret’s syndrome is a rare entity with limited evidence to favor one approach to management over another. In this case, we review the diagnostic and therapeutic options for this rare form of small bowel obstruction.