Cutaneous squamous cell carcinoma (cSCC) is a recognized but infrequent complication of hidradenitis suppurativa (HS). After performing a thorough literature review of all the published cases of cSCC developing in HS, we identified that White males who are smokers and afflicted with severe gluteal or perianal HS are more likely to develop cSCC. Human papillomavirus (HPV) was found to be a common co-factor. cSCC of ulcerative morphology with a poorly differentiated histologic grade, the presence of nodal or distant metastasis, and recurrent cSCC were associated with decreased survival. Regular screening of suspicious lesions for detection of cSCC in patients with HS, notably those with the aforementioned demographics, is highly recommended.