Alopecia in a human immunodeficiency virus (HIV) population requires a broad differential. We present a case of alopecia in an HIV-infected patient with a recent history of latent syphilis that was clinically consistent with alopecia areata (AA). Ultimately, biopsy demonstrated AA, and the patient responded to intralesional steroid injections. The occurrence of AA, an autoimmune disease with perifollicular inflammation of predominantly CD4+ and CD8+ cells, in HIV infection has been described in a few case reports, and our case highlights the importance of the biopsy. We will explore the association of autoimmunity and HIV and the various theories into the pathogenesis of AA in the HIV population.