Diagnosis in secondary syphilis remains challenging because of the diversity of clinical presentations. The most commonly observed cutaneous presentation is a generalized, non-pruritic, papulosquamous eruption varying from pink to violaceous to brown, with mucous membrane involvement. The diagnostic methods used to identify secondary syphilis are the same as those used to diagnose other stages of syphilitic infection. The persistence of syphilis in both developed and underdeveloped regions highlights the importance of considering syphilitic infection in the setting of a cutaneous pustular eruption, especially one that fails to respond to standard therapy. Testing for other sexually transmitted diseases, including HIV, should be performed in all patients diagnosed with syphilis.