Scrotal masses encompass a heterogenous group of conditions affecting the skin and soft tissue of the scrotum or underlying testis, ranging from benign to malignant and from indolent to conditions requiring urgent medical evaluation.Accurate and timely diagnosis is imperative with scrotal masses, as the medical ramifications of different diagnoses vary widely, and the social and psychological implications can be significant. Here we present the first reported case of a middle-aged male with an enlarging scrotal/extra-testicular mass, which upon excision, was found to be consistent with a proliferating trichilemmal tumor, a benign neoplasm derived from outer root sheath of the hair follicle which has a strong capacity to simulate squamous cell carcinoma. Distinguishing between these two entities is of utmost importance due to their significantly different prognostic and treatment ramifications, and ultimately directs appropriate management of these patients.