Cutaneous squamous cell carcinoma (cSCC) is one of the most common cancers in the United States. Outcomes are generally favorable, but a subset of cSCC is biologically distinct and requires a different approach because of its higher risk of local recurrence, metastasis, and death. This article focuses on the recent literature regarding identification of this high-risk subset, efforts to validate and improve the prognostic ability of staging systems, and updates in management.