Squamous cell carcinoma (SCC) is a rare finding in the adolescent population, with most cases occurring in patients with underlying heritable diseases or immunologic conditions. Moreover, the incidence of oral SCC in this age group is extremely low. While isolated cases of adolescent oral SCC have been documented, most have been primary tongue or lip lesions. We report 4 cases of gingival SCC occurring in otherwise healthy adolescent patients. The preliminary clinical impressions ranged from factitial injury to inflammatory tissue. Microscopic similarities, including overlap with pseudoepitheliomatous hyperplasia and keratoacanthoma, were seen. Review of the literature indicates that adolescent gingival SCC is extremely rare and a challenging diagnosis for the clinician and pathologist alike. Diagnostic pitfalls, possible etiologic factors, and the prognostic outlook of this condition are discussed.