Gallstones are a very uncommon cause of obstruction at any site of the gastrointestinal tract and commonly affect the elderly. The mechanism by which the stones pass into the intestine is a biliary-enteric fistula, more often after an episode of acute cholecystitis. Radiologic studies may prove very helpful in diagnosis, but a high index of suspicion and accurate medical history are also warranted. We present the case of a 77-year-old patient who was admitted with signs of acute cholecystitis. During his hospitalization, he developed symptoms of small bowel obstruction. Imaging studies revealed an obstacle in the proximal intestine and the patient underwent exploratory laparotomy which identified a 5 cm gallstone lodged in the proximal jejunum; an enterolithotomy was performed. Surgical options in such cases are affected by the general condition of the patient and the extent of the inflammatory and ischemic process at the affected organs. Despite developments, this clinical entity still carrries high mortality rates. This could be attributed to the comorbidities of the elderly and the fact that it remains a rare and difficult diagnostic entity.