Malignant syphilis (lues maligna) is a rare form of secondary syphilis, first described by Bazin in 1859, frequently associated with HIV infection. The resurgence of syphilis in the recent times has been attributed to rise in HIV infection. Malignant syphilis is characterized by the presence of pleomorphic multiple round-to-oval papules, papulopustules, or nodules with ulceration, without central clearing, and occasionally exhibit a lamellate brown to black rupioid crust with prodromal symptoms. We herein report a case of early malignant syphilis in a young immunocompromised patient who was HIV positive and noncompliant to antiretroviral therapy, from Northeast India. The HIV/AIDS epidemic is rising at an alarming rate in this part of the country which has thus led to an increase in the number of other sexually transmitted infections.