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Spontaneous pneumothorax (SP) is uncommon and can present as a primary disease process or as a result of underlying lung pathology. Several parenchymal lung diseases, such as malignancy, are known to cause SP. One such malignancy, angiosarcoma, has a high propensity to metastasize to the lung and present as cavitary and cystic lesions.We present a case of a 76-year-old male diagnosed with angiosarcoma of the scalp that was found to have extensive cystic pulmonary metastatic lesions. Soon after his initial diagnosis, he presented with severe respiratory distress secondary to a spontaneous left-sided pneumothorax. After intubation and left-sided chest tube placement, the patient developed a right-sided tension pneumothorax requiring emergent chest tube placement.Cutaneous angiosarcoma is a rare malignancy that frequently metastasizes the lung. Spontaneous pneumothorax can be the presenting manifestation of the disease and often results in respiratory failure.