Wallenberg’s syndrome, also known as posterior inferior cerebellar artery syndrome (lateral medullary syndrome), is known to be a common cause of posterior ischemic stroke syndromes in men in their 60s and may present with varied symptoms devoid of focal neurological signs making it easily missed as a differential of posterior ischemic strokes. It involves a stroke in the vertebral or posterior inferior cerebellar artery of the brainstem. In this case report, we critically examine the case of a 66-year-old man with newly diagnosed diabetes whose main presentation was dysphagia and unsteady gait. There was no motor or sensory examination finding in our patient, and the initial computed tomography of the brain was negative for any intracranial pathology leading to very low suspicion of stroke. However, given a high index of suspicion and a thorough oropharyngeal examination ruling out structural abnormality, magnetic resonance imaging of the brain revealed features suggestive of Wallenberg’s syndrome. This case emphasizes careful consideration of posterior stroke syndrome when evaluating patients presenting with dysphagia without typical motor/sensory symptoms of cerebrovascular accident and the requirement of further imaging to support the diagnosis.