We present the case of a man in his thirties who had attended the emergency department with complaint of a distressing headache and associated intermittent facial droop with occasional slurred speech. The patient’s symptoms were bizarre in their nature as they were random, not sustained and he had long intervals when he was asymptomatic and was his normal self. During the course of admission his symptoms evolved resulting in neurological deficits which were more sustained, prompting the need for further imaging beyond the initial plain CT brain which showed no abnormality. This led to the diagnosis of vertebral artery dissection (VAD) complicated with an ischaemic stroke in the posterior inferior cerebellar artery distribution (PICA) on MRI/MRA. Dual anti-platelet treatment was commenced with the patient attaining gradual symptomatic improvement prior to discharge. He has reported some degree of neurological sequelae which he described as intermittent poor coordination on follow up visit in clinic after discharge.