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Raynaud's phenomenon of the nipple (RPN) is a cause of nipple pain scarcely reported in the literature and frequently missed by physicians. We present a case of RPN in a pregnant mother who sought breast surgical consultation for episodic nipple pain. Review of the literature reveals RPN is predominant in lactating and pregnant patients and missed diagnosis can cause cessation of breastfeeding or mistreatment with antifungals. Clinical suspicion should be raised if symptoms are precipitated by cold, associated with color change, occur during pregnancy or breastfeeding, or with a history of Raynaud's. Treatment is generally supportive, with nifedipine used for severe cases.