Several countries experience a new epidemic of syphilis, mainly due to the changes in risk behaviors. Dermatologists play an important role in the diagnosis, since cutaneous manifestations are frequent during disease progression. We report a rare case of secondary syphilis with periungual involvement. Syphilis, especially in the secondary form, may present with different clinical features, affecting different organs, and mimicking many diseases. Although nail apparatus lesions are more common in the primary form of the disease, they may also be present in the secondary and tertiary forms. Therefore, a comprehensive knowledge of the diverse forms of syphilis presentation is important for an early diagnosis and timely treatment.