Obstructed labor is a common complication of human childbirth. In parts of the world where access to emergency obstetric services is limited, obstructed labor is a major cause of maternal mortality. Women who survive the ordeal of prolonged obstructed labor often end up suffering from an obstetric vesicovaginal fistula or another serious birth injury that leaves them crippled for life. Compared with the other higher primates (chimpanzees, bonobos, gorillas, and orangutans), these problems are uniquely human. This article reviews the evolutionary origins of the human obstetric dilemma with special reference to the changes imposed on pelvic architecture by the assumption of upright, bipedal posture and locomotion. The subsequent development of progressively increasing brain size (encephalization) in hominins led to the present human obstetrical conundrum: how to balance the evolutionary advantage of bigger babies with larger brains against the presence of a narrow pelvis that is difficult for a fetus to traverse during labor.