Here we present a case of a 38-year-old Indian man with a history of extramarital relationships who presented with pleurisy, skin rash, and radiological findings of pleural effusion. After thorough investigation of the etiology of his acute illness, he was found to be positive for syphilis. Review of literature revealed a small number of case reports of pleural effusion as a manifestation of secondary syphilis. The review of criteria proposed in the literature was utilized to diagnose this patient as a case of pulmonary syphilis.