This is a case of a 35-year-old Gravida 5 Para 5 (5005) who underwent curettage for retained placental fragments after delivering her fifth child. Within 16-month postpartum, the patient had nonspecific occasional abdominal pain and oligomenorrhea. Imaging studies revealed a uterine defect with a bowel segment passing through. A referral to a tertiary-level hospital was made. Hysteroscopy was attempted; however, an obliterated cervical canal was encountered. Laparoscopy revealed a 10 cm ileal segment completely herniating into a 2.5 cm uterine defect at the posterior uterine wall. Laparoscopic enterolysis followed by hysterectomy, extracorporeal resection, and anastomosis of the involved ileal segment was performed. This is an uncommon case of an iatrogenic uterine perforation following curettage after a term pregnancy. Its unique clinical presentation and intraoperative findings resulted in an equally unique array of surgical approach.