Secondary syphilis has been known since the late 19th century as the great imitator; however, some experts now regard cutaneous lymphoma as the great imitator of skin disease. Either disease, at times an equally fastidious diagnosis, has reported to mimic each other even. It is thus vital to consider these possibilities when presented with a patient demonstrating peculiar skin lesions. No other manifestation of secondary syphilis may pose such quandary as a rare case of rupioid syphilis impersonating cutaneous lymphoma. We present such a case, of a 36-year-old HIV positive male, misdiagnosed with aggressive cutaneous lymphoma, actually exhibiting rupioid syphilis thought secondary to immune reconstitution inflammatory syndrome (IRIS).