In this case of secondary syphilis, pustular lesions progressed rapidly to painful ulcerative lesions in a patient with early HIV infection. This rapidly progressive form of early syphilis has historically been called lues maligna praecox, a severe form of noduloulcerative secondary syphilis. Serologic tests for syphilis were positive and biopsy showed forms consistent with Treponema pallidum in the lesions. This case demonstrates how HIV infection may affect presentation and diagnosis of secondary syphilis.