Cesarean birth is the most common surgical procedure in the United States, accounting for up to one-third of all births nationally. Compared to vaginal delivery, cesarean section is associated with higher rates of maternal morbidity and mortality. The nuances of obstetric surgery contribute to major surgical complications that develop during this routine surgical procedure including postpartum hemorrhage, hysterotomy extension, uterine inversion, and post-cesarean infection. Postpartum hemorrhage is a leading cause of maternal mortality worldwide with uterine atony as the main underlying etiology. Management relies on pharmacologic therapy in addition to surgical interventions such as balloon tamponade, arterial ligation, uterine artery embolization, and cesarean hysterectomy. Alternatively, extension of the hysterotomy and uterine scar dehiscence disrupt surrounding vital structures and contribute to hemorrhage-related maternal morbidity. Surgical techniques to identify and repair these extensions are discussed. Uterine inversion is a rare and often unexpected obstetrical emergency that is associated with substantial maternal morbidity. Corrective measures described include manual replacement as well as surgical techniques such as the Huntington and Haultain procedures. Lastly, the nature of cesarean delivery is a source of pelvic infectious morbidity. Common puerperal microbes, best practice recommendations for infection prevention, and evidenced-based surgical techniques are reviewed.