The diagnosis of secondary syphilis can be challenging due to its various clinical and histopathological presentations. A late or incorrect diagnosis can result in disease progression with consequent morbidity or mortality. Due to the importance of a correct diagnosis and specific treatment, it is of the utmost importance for healthcare providers to consider the various manifestations of syphilis. We describe an atypical presentation of secondary syphilis in an African American man infected with HIV and chronic psoriasis, who presented with two months of diffuse maculopapular rash and new visual changes, found to have acute syphilitic placoid chorioretinitis (ASPCC) and a psoriasis vulgaris flare.