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Stevens-Johnson Syndrome (SJS) and Toxic Epidermal Necrolysis (TEN) are adverse cutaneous drug reaction that has been associated with various drugs like antibiotics, anticonvulsant and non-steroidal anti-inflammatory agents. Fluconazole has rarely been associated with SJS and TEN. A 39-year-old male patient of SJS due to fluconazole, who was subsequently diagnosed to suffer from Acquired Immunodeficiency Syndrome (AIDS) is being reported. The low CD4+ T Cell count in this patient is a likely contributing factor for the precipitation of SJS due to fluconazole. There is a paucity of reports of SJS due to fluconazole in HIV positive patients, though TEN has been described in few patients. This case highlights that fluconazole causing SJS/TEN is more likely in a HIV positive patient. This patient’s HIV positive status was diagnosed subsequent to the diagnosis of SJS.