This middle-aged heterosexual man with no history of immune suppression presented multiple times over the course of a few months to the emergency department and the local general practitioner with recurrent predominantly left-sided intermittent headaches. Non-specific changes on non-contrast CT brain (not uploaded) raised the possibility of subacute cerebral infarction and a raised ESR pointed the managing clinicians towards a presumptive diagnosis of vasculitis. Following the presented MRI findings, serological and cerebrospinal fluid testing yielded a positive result to anti-treponemal antibodies, in keeping with neurosyphilis. HIV testing and vasculitis serological panel were negative. The patient went on to receive long term intravenous antibiotics as per best practice and remains under ongoing follow-up with the neurology and infectious diseases teams.