The objective of this study was to describe risk factors and recurrence patterns that can guide the creation of evidence-based surveillance guidelines for advanced cutaneous squamous cell carcinoma of the head and neck. This was a single-institution retrospective case series. High-volume academic head and neck surgical oncology practice. Patients who underwent surgery for cutaneous squamous cell carcinoma of the head and neck staged Brigham and Women's Hospital T2b and T3 from 2003 to 2023 were reviewed. Patient demographics, clinicopathologic history, cancer data, treatment, and outcomes were abstracted. Disease-free survival and risk factors for recurrence were described. A total of 183 patients were included. Fifty-six (30.6%) experienced recurrence. This included local recurrence in 21 (11.5%), regional in 21 (13.3%), and distant in 11 (6%). The majority of regional and distant recurrences occurred within 1 year of surgery. The majority of disease recurrence occurs in the first 1 to 2 years following surgical excision of advanced-stage cutaneous squamous cell carcinoma of the head and neck. Close surveillance and frequent imaging within those years are critical to catch subclinical and distant diseases.