Raynaud's phenomenon of the nipple is an unusual cause of severe nipple pain. Precipitants for Raynaud's phenomenon of the nipple are known to be cold temperatures, caffeine, and emotional stress. Nipple pain is quoted as the most common cause of cessation of breastfeeding. It is important that lactation consultants and other health care professionals are aware of Raynaud's phenomenon of the nipple and the treatment options available. This is a case of a 37-year-old woman, Gravida 2, Para 1, who was first seen in the antenatal clinic at 34 weeks gestation. A diagnosis of Raynaud's phenomenon of the nipple was made after she began taking labetalol for pregnancy-induced hypertension. The phenomenon had occurred in both of her previous pregnancies on commencing labetalol and resolved postnatally on cessation of the drug. We aim to raise awareness of both the condition itself and the potential role of labetalol in the development of Raynaud's phenomenon of the nipple.