The formation of a milk bleb during breastfeeding is frequently associated with nipple pain that may affect the breastfeeding success of the mother-infant dyad. Early cessation of breastfeeding may occur when pain is ongoing. Timely evaluation and diagnosis and effective management are imperative to prevent tissue damage and lingering symptoms. In this case report, we evaluate the unique challenges of the diagnosis and management of milk blebs, including nonpharmacologic and pharmacologic treatment.