Physicians should be aware of unusual presentations of syphilis. For dermatologists, the visual recognition of lesional morphology and distribution is a fundamental part of clinical evaluation, which dictates the workup and diagnosis. Secondary syphilis has a variety of presentations, the most common being a diffuse symmetrical papulosquamous eruption. It continues to be a diagnostic challenge as the myriad manifestations of secondary syphilis can mimic many dermatological disorders. Herein we report a case of secondary syphilis with an uncommon presentation characterized by disseminated annular and arcuate lesions.