The clinical features of syphilitic lesions in the oral mucosa are variable, and there are no specific guidelines in the scientific English literature for dental practitioners regarding oral signs and symptoms that mandate serological tests for syphilis. We performed an updated review of reports on protocols for managing acquired oral syphilis (AOS) and offer recommendations with an emphasis on clinical features. We also add two new cases from our own files. Our analyses of global reports revealed that males are significantly more often affected than females, and their mean age is higher. Young adults are most affected, with a peak in the third and fourth decades of life. Ulcers and mucous patches as manifestations of AOS are the most prevalent clinical features in the oral mucosa. Mucous patches are significantly more prevalent in females as compared to males and tend to present as multiple rather than isolated lesions, while ulcers frequently appear as a sole lesion. The tongue, lip, and palate are the most affected anatomical sites. New oral lesions in the context of unprotected sexual intercourse warrant serological testing for syphilis.