Dermoscopy is non-invasive tool as a diagnostic adjunctive in clinical dermatology. It demonstrates definitive features in infective and inflammatory dermatoses. Syphilis is emerging again as newly diagnosed cases are being reported and treated across the country. There is a sparsity in the dermoscopic reports in syphilis. It shows characteristic patterns in primary and secondary syphilis. However, dermoscopic monitoring of syphilitic lesions is lacking in the literature. Here, we report cases of syphilis with treatment monitoring by dermoscopy.