A 57-year-old woman presented with a 5-day history of worsening right upper quadrant pain, bilious emesis and approximately 20 pounds of weight loss. The patient was afebrile, without jaundice and had mild tenderness in her right upper quadrant. She noted an incidental finding of asymptomatic cholelithiasis on imaging 4 years earlier. An abdominal radiograph revealed pneumobilia and a large ectopic calculus. An abdominal CT scan confirmed pneumobilia, a large concretion completely obstructing the third portion of the duodenum and a soft tissue communication between the gallbladder and proximal duodenum. She was brought to the operating room for definitive treatment and had the obstructing gallstone removed via a transverse duodenotomy. Bouveret syndrome is a rare cause of small bowel obstruction that requires a high index of suspicion for diagnosis. It should be considered in older patients with clinical evidence of gastric or duodenal obstruction, particularly with a history of cholelithiasis.