Breastfeeding benefits both infant and maternal health. Use of epidural anesthesia during labor is increasingly common and may interfere with breastfeeding. Studies analyzing epidural anesthesia's association with breastfeeding outcomes show mixed results; many have methodological flaws. We analyzed potential associations between epidural anesthesia and overall breast-feeding cessation within 30 days postpartum while adjusting for standard and novel covariates and uniquely accounting for labor induction. A pooled analysis using Kaplan-Meier curves and modified Cox Proportional Hazard models included 772 breastfeeding mothers from upstate New York who had vaginal term births of healthy singleton infants. Subjects were drawn from two cohort studies (recruited postpartum between 2005 and 2008) and included maternal self-report and maternal and infant medical record data. Analyses of potential associations between epidural anesthesia and overall breastfeeding cessation within 1 month included additional covariates and uniquely accounted for labor induction. After adjusting for standard demographics and intrapartum factors, epidural anesthesia significantly predicted breastfeeding cessation (hazard ratio 1.26 [95% confidence interval 1.10, 1.44], p < 0.01) as did hospital type, maternal age, income, education, planned breastfeeding goal, and breastfeeding confidence. In post hoc analyses stratified by Baby Friendly Hospital (BFH) status, epidural anesthesia significantly predicted breastfeeding cessation (BFH: 1.19 [1.01, 1.41], p < 0.04; non-BFH: 1.65 [1.31, 2.08], p < 0.01). A relationship between epidural anesthesia and breastfeeding was found but is complex and involves institutional, clinical, maternal and infant factors. These findings have implications for clinical care and hospital policies and point to the need for prospective studies.