Epithelioid Hemangioendothelioma (EH) is a rare soft-tissue tumor which may present as an isolated tumor or can spread to affect internal organs. The course of EH varies, based on the tissue of origin. This case report describes a young woman who developed cutaneous EH with concurrent intracranial disease during pregnancy. After resection, the lesions returned. Even after several courses of chemotherapy and radiotherapy, the patient developed multifocal disease including pulmonary, skeletal, and liver disease. She now exhibits stable disease after approximately 6 years of therapy with lenalidomide.