Known as “the great imitator,” secondary syphilis may clinically manifest itself in myriad ways, involving different organs including the oral mucosa, and mimicking, both clinically and histologically, several diseases, thereby making diagnosis a challenge for clinicians. We highlight the clinical aspects of oral manifestation in 7 patients with secondary syphilis. Clinicians should consider secondary syphilis in the differential diagnosis of ulcerative and/or white oral lesions.