The importance of breastfeeding is well recognised with benefits for both the mother and infant. Despite these benefits, women often cease breastfeeding prematurely after experiencing common problems such as breast and nipple pain or low breast milk supply in the early weeks of breastfeeding. Some mothers stop breastfeeding while taking medications to treat these conditions because of unfounded concern or inappropriate advice from healthcare providers. Most of these conditions can be managed without the need to stop breastfeeding. This review provides pharmacists with an understanding of common breastfeeding problems and outlines evidence-based pharmacological management strategies for women experiencing these complications. All health professionals need to support mothers to continue breastfeeding for as long as they desire, and pharmacists have a unique role and a clear responsibility to provide up-to-date, evidence-based information to empower breastfeeding mothers in their decision making to ensure breastfeeding is not stopped without good reason.