Cutaneous malignancies of the head and neck are common; however, superficial sarcomas of the head and neck are relatively rare. We present a 71-year-old unhoused gentleman with challenging access to medical care and poor health literacy who presented with a large, isolated, pedunculated mass of the left auricular helix. Preoperative biopsy was compatible with pleomorphic dermal sarcoma (PDS). The patient subsequently underwent definitive surgical resection with partial auriculectomy and bilateral advancement flap closure. Final pathology confirmed the diagnosis of PDS. Given the rarity of PDS of the ear, we describe a challenging case presentation, diagnosis, and management in an unhoused patient.