Head and neck cutaneous squamous cell carcinoma (HNCSCC) is a growing problem in the immunosuppressed population, and the behavior of these cancers can be unexpectedly aggressive. The role of adjuvant radiation therapy (RT) in the management of high-risk HNCSCC has been an area of much debate. We present a case of HNCSCC with perineural invasion (PNI) successfully treated with surgery and adjuvant RT to prevent recurrence.