Mechanical small bowel obstructions caused by gallstones account for 1% to 3% of cases. In these patients, 80% to 90% of residual gallstones in these patients will pass through a remaining fistula without consequence. Recurrent gallstone ileus has been reported in 5% of patients. We report the case of a woman, aged 72 years, who presented with mechanical small bowel obstruction caused by gallstone ileus. After successful surgical therapy for gallstone ileus, the patient's symptoms recurred, and she was diagnosed with recurrent gallstone ileus requiring a repeat operation. While management of gallstone ileus can be achieved through a single-stage operation including enterolithotomy and cholecystectomy with repair of biliary-enteric fistula or by enterolithotomy alone, the literature supports enterolithotomy alone as the treatment of choice for gallstone ileus due to decreased mortality and morbidity. However, the latter approach does not obviate potential recurrence. We present this case of recurrent gallstone ileus to elucidate and review the pathogenesis, presentation, diagnosis, and consensus recommendations regarding management of this disorder.