Cutaneous squamous cell carcinoma (cSCC) is the second most common nonmelanoma skin cancer worldwide. Cutaneous squamous cell carcinoma can potentially be treated fully with minimal morbidity when detected early; however, certain subtypes of cSCC have been shown to confer a poorer prognosis for patients. In these high-risk tumors, increased incidence of recurrence, as well as metastasis to local lymph nodes and distant sites, is seen as a result of certain patient characteristics and pathological features. While guidelines regarding the management of high-risk cSCC have been produced, no clear consensus management or prognostic algorithms exist. In this review, we discuss current definitions of high-risk cSCC, recommendations regarding the management of cSCC, and current guidelines.