Squamous cell carcinomas (SCCs) often arise secondary to UV-induced DNA damage resulting in genetic mutations, but can also occur in the setting of prolonged inflammation. Folliculitis decalvans (FD) is a rare cicatricial alopecia with a complex, multifactorial pathogenesis that results in chronic inflammation and scarring. We present a patient with severe, chronic FD who developed metastatic squamous cell carcinoma of the scalp.