This article identifies how mode of delivery and the presence of labor affect the initiation and effectiveness of breastfeeding. This is a retrospective cohort study of breastfeeding success after vaginal delivery, cesarean section after labor, and scheduled cesarean section in term, singleton deliveries in nulliparous patients at a large academic institution from 2017 to 2018. Exclusion criteria included major postpartum complications requiring admission to the surgical intensive care unit or neonatal intensive care unit, general anesthesia, and major fetal anomalies. Breastfeeding success in the immediate postpartum period, defined as the first 2 to 3 days postpartum prior to hospital discharge, was measured by the presence of breastfeeding, the need for formula supplementation, the average number of breastfeeding sessions per day, the average amount of time spent at each breastfeeding session, the average number of newborn stools and wet diapers produced daily, and the neonatal percentage in weight loss over the first 2 to 3 days of life. Multivariable linear and logistic regression were used to assess the association between mode of delivery and markers of breastfeeding success after adjusting for potential confounders. A Tukey's post hoc analysis with pairwise comparisons was performed to assess differences in breastfeeding outcomes between vaginal delivery, scheduled cesarean section, and cesarean section after labor. A total of 2,966 women met inclusion criteria during the study period, 1,936 (65.3%) of whom underwent spontaneous vaginal delivery, 415 (14.0%) of whom delivered by scheduled cesarean section, and 615 (20.7%) of whom underwent cesarean section after labor. There were significant differences in maternal age, obesity, race/ethnicity, insurance status, gestational age at delivery, birth weight, and 1-minute Apgar's score less than 7 between vaginal delivery, scheduled cesarean section, and cesarean section after labor. There were also significant differences between indication for oxytocin, type of anesthesia, and postpartum hemorrhage between the three groups. After controlling for these factors, women who underwent vaginal delivery were more likely to have infants with decreased need for formula supplementation (adjusted odds ratio [aOR] = 1.71, 95% confidence interval [CI]: 1.52-1.93) and were less likely to switch from breast to formula feeding (aOR = 1.71, 95% CI: 1.04-1.31) in comparison to women who delivered via cesarean section in labor or scheduled cesarean section. The infants of these women also had an increased number of breastfeeding sessions on average (β = 0.06, p = 0.002), required fewer number of daily formula feedings (β = 0.14, p < 0.001), and experienced a smaller percentage in neonatal weight loss over the first 2 to 3 days of life (β = 0.18, p < 0.001) compared to those born after cesarean section and cesarean section after labor. These women comparatively required less time at each breastfeeding session (β = 0.06, p = 0.005), and produced fewer wet diapers and stools on average (β = 0.12, p < 0.001 and β = 0.12, p < 0.001, respectively). On post hoc analysis with pairwise comparisons, and on separate sensitivity analysis of only women who underwent cesarean delivery, there was no difference in breastfeeding outcome measures between scheduled cesarean section and cesarean section in labor. Women who deliver by cesarean section, despite the presence or absence of labor, are less likely to maintain exclusive breastfeeding postpartum and are more likely to require formula supplementation. These women may need more support with breastfeeding after surgery in order to experience similar benefits for neonatal growth and weight gain. · Women who deliver by cesarean section are less likely to maintain exclusive breastfeeding.. · Women who deliver by cesarean section are more likely to require formula supplementation.. · Women may need more support with breastfeeding after cesarean delivery..