Rectal prolapse associated with intussusception is when the intestine slides into the adjacent part causing a protrusion through the anus. It is also referred to as recto-anal intussusception or trans-anal protrusion of intussusception. Pre-operative diagnosis of the associated intussusception is usually hard to make. We present a case of a patient who presented with a rectal prolapse. Surgical exploration also noted an intussusception and rectal malignancy. We demonstrate the importance of surgical management in patients with rectal prolapse to avoid progression of a malignancy or intussusception.