A 31-year-old woman who had successfully undergone bariatric surgery (gastric bypass with Roux-en-Y anastamosis) three years earlier presented with complaints of acute epigastric abdominal pain, nausea, and vomiting. Computed tomography (CT) showed small bowel intussusception, and the patient was taken to the operating room. A mass the size and shape of a football was found; the mass consisted of the proximal limb of the Roux-en-Y intussuscepted in a retrograde manner. The bowel was gently reduced, deemed viable, and the Roux-en-Y anastamosis was revised with resection of the lead point. We urge the surgeon to be highly suspicious of acute bowel obstruction in the post-bariatric surgery population and believe that CT is essential in evaluating these patients. We further recommend resection of the lead point to avoid repeat bouts of intussusception from the same focal etiology.