Uncommon causes of small bowel obstruction can provide interesting surgical decision-making challenges. This report describes a patient with recurrent gallstone ileus. According to most current reviews, erring on the side of enterolithotomy alone as the treatment of choice for gallstone ileus appears to be the most appropriate decision. Although a rare scenario, the situation of recurrent gallstone ileus presents an interesting learning opportunity. It is important to keep in mind the need for complete examination of the abdomen. Furthermore, evacuation of any remaining stones from the gallbladder is imperative if possible. Erring on the side of enterolithotomy alone as the treatment of choice for gallstone ileus has been shown to be a safe and effective treatment decision over a single-stage removal of the stone with closure of the cholecystoduodenostomy.