Angiosarcoma is a rare malignant entity that typically presents as a rapidly progressing ecchymotic or cellulitis-like lesion with subsequent bleeding or ulceration. Atypical presentations have been described, such as cases mimicking rosacea, making the diagnosis more challenging. Due to the high rate of local recurrence, metastasis, and disease-specific mortality, early identification and treatment is critical. Here we describe a 69-year-old man with a vascular targetoid lesion clinically consistent with a targetoid hemosiderotic hemangioma (THH); however, biopsy was consistent with an angiosarcoma. Early diagnosis of this lesion resulted in prompt wide local excision and no detection of metastasis. This case report highlights the importance of thorough evaluation of new onset vascular lesions and the unique THH-like presentation of an angiosarcoma.