Although most skin cancers of the head and neck are successfully treated by a variety of practitioners using an array of modalities, aggressive cutaneous squamous cell carcinoma demands a multidisciplinary approach and are commonly encountered in an otolaryngology practice. The challenge lies not only in recognizing dangerous lesions early but also in delivering effective treatment with rapidly emerging evidence, new therapeutic modalities, and dynamic consensus guidelines. Even the ongoing clinical and pathologic staging systems for this disease evolve apace of editions of the AJCC staging manual. cSCC constitutes an emerging epidemic with a potential incidence of 750,000 cases in the United States, costing a significant portion of the over $5.4 billion in annual treatment expenditure for nonmelanoma skin cancer (NMSC). Aggressive cSCC are prone to regional lymph node metastases, perineural invasion, and recurrence, which create significant morbidity and disease-specific mortality in select patients, particularly those who are immunocompromised. Clinical challenges with collaboration (versus competition) with other dermatologic surgeons, management of the draining lymphatics (including sentinel lymph node biopsy), judicious use of advanced reconstructive techniques, indications for radiation therapy, and the applications of newer systemic therapies are encountered across head and neck surgical practices. Recently published studies have demonstrated the utility of immunotherapy in select patients with locally and regionally advanced cutaneous squamous cell carcinoma, with >50% pathologic complete response rates reported when used in the neoadjuvant setting. This panel will use clinical cases to provide an update to practicing otolaryngologist-head and neck surgeons on the evaluation, staging, clinical decision making, and treatment considerations in cutaneous squamous cell carcinoma of the head and neck.