Cutaneous angiosarcoma is a rare aggressive malignancy of vascular origin that usually arises in the scalp or face of elderly men. We describe a case of primary cutaneous angiosarcoma with skin metastases and presumed metastases to the lung in a 58-year-old man who presented with persistent bloody pleural effusions, an asymptomatic nontraumatic red patch on the forehead of 2 to 3 months' duration, and a pair of purpuric papules on his left mid back of unknown duration. Cutaneous metastases of angiosarcoma are uncommon. Spontaneous persistent bloody effusions without hemoptysis are distinctly uncommon, and pleural fluid cytology is repeatedly negative in lung or pleural angiosarcoma, making it difficult to diagnose without tissue biopsy.