Syphilis has been labelled as a 'Great Imitator'. The clinical manifestations of syphilis are largely mucocutaneous lesions, thus dermatologists are well placed to be able to diagnose it. However, the secondary stage of syphilis can have myriad presentations, and can easily be misdiagnosed even by an experienced dermatologist. The dermatologists should be aware of rarer morphological variants of the disease.