Gallstone ileus (GSI) is an uncommon entity that causes obstruction of the intestinal lumen due to gallstones. It affects mainly the elderly with multiple comorbidities, leading to a high mortality rate. In this case, an 81-year-old woman was admitted due to GSI. She had a recurrence after 5 days of the index surgery. Recurrent intestinal obstruction due to GSI during the same hospitalization despite complete clearance of the small bowel from stones is rare. Through our case, we will discuss management along with a review of the current evidence.