Atypical ductal hyperplasia of the breast is a benign proliferative condition that is associated with an increased risk of development of breast cancer in either the ipsilateral or contralateral breast. Following diagnosis at biopsy, respective management options range from observation to chemoprophylaxis to prophylactic surgery. We present two cases in young women, facing prolonged follow-up, one managed with observation only, and the other managed with ipsilateral mastectomy and reconstruction.