The mode of delivery in twin gestation has long been a matter of debate. The Twin Birth Study provided caregivers with answers to some of the questions. In patients with twin gestation between 32 and 38 weeks of gestation, with the first twin in cephalic presentation, that match the inclusion criteria of the TBS, the neonatal and maternal outcomes of a planned trial of vaginal delivery are not different than those associated with a planned cesarean delivery. Yet, gestational age at birth, estimated fetal weight and weight difference between the twins, presentations, chorionicity, parity, onset of labor, and caregiver’s experience are some of the many factors that may influence the decision regarding the mode of delivery, the likelihood of a successful vaginal birth, and the outcome of birth in multiple pregnancies. In this chapter, we will provide an up-to-date review of the literature on this topic and address the abovementioned questions.