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Cutaneous squamous cell carcinoma (cSCC) is a common neoplasm in fair-skinned individuals. Its clinical management requires appropriate histological diagnosis, risk stratification, and an individualized selection of imaging studies. This review summarizes the key aspects of cSCC staging and the selective indication for sentinel lymph node biopsy, integrating the most relevant classification systems (AJCC-8, BWH, UICC-8) and the main prognostic factors. Current recommendations on the use of imaging and the criteria for considering a cSCC as locally advanced or high-risk are also reviewed. The evidence is based on national and international guidelines published between 2015 and 2025.