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Syphilis is a sexually transmitted infection caused by a spirochete, which if left untreated, transforms through four stages. Numerous cutaneous manifestations present from the time of the initial infection and evolve as the disease systemically progresses. Syphilis has been around for centuries, and we can attribute the rise of the specialty of dermatology to its prevalence and protean nature. Syphilis is on the rise again for the first time since the advent of penicillin, making it important for healthcare providers to have knowledge of its presentation in its various stages.