Cutaneous angiosarcoma (CA) is a rare form of cancer with limited treatment options and has a very severe prognosis. In this case report, a differential diagnosis, ranging from infection and neoplasia to autoimmune disease, was attributed to recurrent cellulitis centered on a purple lesion. The continuous pursuit of a diagnosis and treatment plan had to be tailored in accordance with patient goals of care. Careful anticipation of disease progression and complications was required following the diagnosis of CA and involved careful transition from palliation to hospice care. Given the aggressive nature of CA, the radical treatment required, and poor prognosis, clinical providers face a difficult task of balancing diagnostic and therapeutic steps with patient goals of care.