Lupus vulgaris represents a type of cutaneous tuberculosis that, if not correctly treated, presents a progressive chronic development whose long-term complications include cutaneous neoplasms. We report on a 55-year-old man presenting a 10-year-old ulcerated and bleeding lupus vulgaris lesion on the left cheek containing a squamous cell carcinoma. Reviewing the literature, we search for possible causes of delay in diagnosis that even now allowed therapy only after discovery of the tumoral complication.