A 48-year-old woman presented with peri-menopausal bleeding and was scheduled for a hysteroscopy and D&C. During the procedure, uterine perforation occurred and omental tissues were seen entering the perforation site. A diagnostic laparoscopy the following day confirmed a perforated uterus with no other organ injuries. Uterine perforation is an uncommon but serious complication that can occur during procedures like hysteroscopy, D&C, IUD insertion, and termination of pregnancy. Risk factors include high-risk uteri such as postpartum or pregnant uteri, management depends on the extent of injury and bleeding.