Monoamniotic twin pregnancies are exceedingly rare. These are high-risk pregnancies that present a unique set of challenges for the obstetrician-gynecologist. There is a high risk of intrauterine fetal demise, secondary to co-morbid conditions including, but not limited to, congenital anomalies and umbilical cord entanglement. Successful delivery and favorable neonatal outcomes are predicated on early diagnosis, intensive fetal monitoring, and timely delivery. The management guidelines for these pregnancies rely primarily on retrospective studies and expert consensus, although some substantial conclusions can be made regarding appropriate antepartum and intrapartum care. We present the case of a 38-year-old gravida four, para three, with monoamniotic twins who delivered successfully after inpatient hospitalization at viability, administration of corticosteroids for fetal lung maturity, and vigilant fetal monitoring. We conclude that the combination of early ultrasound, intensive fetal monitoring, and interdisciplinary coordination among generalist obstetrician-gynecologists, maternal-fetal medicine specialists, and nursing staff is paramount for providing the greatest chance of a favorable outcome.