This article identifies problems and conditions that contribute to nipple pain during lactation and that may lead to early cessation or noninitiation of breastfeeding. Signs and symptoms of poor latch-on and positioning, oral anomalies, and suckling disorders are reviewed. Diagnosis and treatment of infectious agents that may cause nipple pain are presented. Comfort measures for sore nipples and current treatment recommendations for nipple wound healing are discussed. Suggestions are made for incorporating in-depth breastfeeding content into midwifery education programs.