Syphilis is an important bacterial infection caused by Treponema pallidum, transmitted through blood transfusion, sexual contact (oral, vaginal, and/or anal), or vertically from mother to child during pregnancy. Recognized as “the great imitator,” syphilis presents with a wide range of clinical manifestations that can mimic many other conditions. It is classified into primary, secondary, early non-primary non-secondary, and unknown duration/late-stage (tertiary), and congenital forms. Primary syphilis is characterized by a self-healing, painless ulcer (chancre) at the infection site. Secondary syphilis presents with systemic symptoms such as fever, malaise, and lymphadenopathy, along with mucocutaneous lesions, including palmoplantar erythematous-brownish plaques and papules. Oral mucosal lesions may include whitish to grayish plaques, nonspecific ulcerations, and erythematous lesions. Unknown duration/late-stage syphilis is rare, but can manifest as aggressive ulcerations leading to palatine perforation or gumma affecting the dorsum of the tongue. Diagnosis requires both treponemal and nontreponemal serological tests. Histopathologically, oral syphilis features a dense plasma cell infiltrate beneath the epithelium and around blood vessels. The mainstay of treatment is parenteral penicillin G. Effective management of syphilis and prevention of its spread require screening, surveillance, counseling, and education as key components of public health strategies.