Lichen sclerosus (LS) is a chronic dermatologic condition characterized by atrophic porcelain-appearing plaques that can cause intense discomfort and eventually lead to destruction of local architecture. Lichen sclerosus most commonly arises in the anogenital area, but up to 20% of cases can present on extragenital skin. Rarely, LS can also present with hemorrhage and bullae; the mechanism by which this occurs is unknown. We report two cases of bullous hemorrhagic LS of the breast arising in 66-year-old and 77-year-old women. Bullous hemorrhagic LS of the breast is exceedingly rare, with few reported cases, and presents a diagnostic challenge to clinicians.