Intussusception is a rare cause of intestinal obstruction, especially in adult populations. Adult intussusception was traditionally thought to occur secondary to a pathological lead point such as a malignancy, inflammatory bowel disease, or anatomic abnormality; for example, a Meckel’s diverticulum. Intussusception is a rare surgical complication post Roux-en-Y gastric bypass. An increase in incidence is found with increasing demand of bariatric surgeries. The exact cause of intussusception is unclear. We present a 86-year-old female with retrograde small bowel intussusception posttotal gastrectomy and small bowel resection with Roux-en-Y reconstruction.