Cutaneous angiosarcoma is a rare, highly malignant vascular tumor with three clinical types. It is predominantly seen in the white-skinned people and rarely dealt with among the colored races. Cutaneous angiosarcoma of head and neck of the elderly is a great mimicker with many clinical presentations. The condition needs to be differentiated from several other common conditions and the diagnosis may be extremely difficult in some cases. Herein, we report the case of a 65-year-old man with type 5 skin who presented with an unusual and extensive involvement of the scalp and face presenting a diagnostic challenge.