Aortic aneurysm formation is a known complication of late syphilis. Here we report a case of37 year old female presented with breathlessness and chest pain.On evaluation ascending aorta aneurysm, descending aorta calcification and aortic regurgitation are identified, later on diagnosed to have syphilis. The diagnosis of the aortic aneurysm due to tertiary syphilis may be challenging due to deceptive clinical presentation and rarity of the disease because of widespread use of antibiotics for the management of earlier stages of syphilis.