While uterine prolapse is not uncommon in postmenopausal women, vaginal rupture and evisceration of small bowel in a patient without prior abdominal or pelvic surgery is a rare entity. We present a case of a 79-year-old woman with a prolonged history of uterine prolapse and rectocele who presented with vaginal rupture with subsequent evisceration and incarceration of her small bowel mandating emergent surgery.