Nodular lesions in syphilis are typical of the late benign stage of the disease. It is a rare clinical manifestation of the said disease with a generalized distribution, involving both skin and mucous membranes. Lesions are more prominent on the upper extremities with a special predilection for the palms and the soles in the early stages. We present a case of a 25-year-old Filipino male with a 5-month history of generalized purplish to violaceous nodules with excoriations and scaling. When co-infected with advanced HIV it may present similarly as malignant secondary syphilis. After administration of Benzathine Penicillin G single dose IM, it is important to frequently assess these patients clinically and serologically for possible treatment failures at 3, 6, 9, 12, and 24 months after therapy.