Background: Bouveret’s syndrome is an uncommon complication of the very common problem of gallstone disease. It consists of obstruction due to impaction of a gallstone in the duodenum, through a cholecysto-duodenal fistula and belongs to the larger group of conditions called gallstone ileus which occur after the development of a fistula between the gallbladder and the gastrointestinal tract. It is associated with a high morbidity and mortality because it occurs mostly in the elderly. Case Report: We recently encountered two such cases of Bouveret syndrome in elderly patients. The diagnoses were not made pre-operatively after considering the clinical features and radiological and endoscopic test. They were both successfully managed surgically. Conclusion: Bouveret’s syndrome is an uncommon entity, diagnosis and management of which remains controversial.