It is difficult to determine what types of procedures should be attempted in patients who have recurrent prolapse. We present a case of recurrent lateral enterocele and rectocele after the patient had undergone multiple surgeries for pelvic organ prolapse (POP), including a vaginal hysterectomy, bladder-neck suspension, anterior colporrhaphy, site-specific rectocele repair, apical mesh implant, iliococcygeus vault suspension, and transobturator suburethral sling procedure. With recurrence, the patient underwent robot-assisted laparoscopic sacral colpopexy, tension-free vaginal tape transobturator sling insertion, rectocele repair, and perineorrhaphy with cystoscopy. She then presented with defecatory outlet obstruction and constipation and subsequently was treated with a stapled transanal rectal resection. The patient returned with continued defecatory dysfunction and a recurrent lateral enterocele and rectocele. The recurrence was treated laparoscopically using a lightweight polypropylene mesh. The postoperative period was uneventful. Two years later, the patient reported decreased defecatory symptoms and no further symptomatic prolapse.