Bouveret’s syndrome is a rare form of gallstone ileus caused by the passage and impaction of a large gallstone through a cholecystoduodenal fistula into the duodenum, resulting in gastric outlet obstruction. It is a rare form of gall stone ileus (1-3% of cases of gall stone ileus; gall stone ileus itself is extremely rare occurring in only 0.3-0.5% of patient with cholelithiasis) and causes significant morbidity and mortality1. It is common in elderly female patients with multiple comorbidities including a history of long standing cholelithiasis, presenting with features of small bowel or gastric outlet obstruction. A high index of suspicion is essential for prompt diagnosis and management. An upper gastrointestinal endoscopy, plain abdominal X-Ray and CT scan often helps in confirming the diagnosis and treatment modalities range from endoscopic retrieval, lithotripsy, laparoscopic procedures and when these fail, open surgery and retrieval of the obstructing stone. Here we present a 79 year old lady with multiple comorbidities along with a long standing history of cholelithiasis who developed Bouveret’s syndrome and discuss the pitfalls in diagnosis and management of this difficult and sometimes challenging condition.