We present a case of a 74-year-old man with marked photodamage who was ultimately diagnosed with telangiectasia macularis eruptiva perstans (TMEP) of the scalp. The diagnosis was made more difficult because of the clinical and histological similarity of this case with an early angiosarcoma. TMEP is a benign and indolent rare subtype of cutaneous mastocytosis presenting clinically with red-brown telangiectatic macules, usually symmetrically distributed over the trunk and extremities. Although most cases are limited to the skin, systemic involvement can occur, and this can be a potentially life-threatening disease. Although also rare, in contrast to TMEP, cutaneous angiosarcoma is a highly malignant vascular tumor with a poor prognosis. This case highlights the importance of including TMEP on the differential diagnosis where vascular lesions of the scalp are observed.