Aortic dissection carries a high mortality of up to 40% at the time of initial dissection and an additional 1% per hour the dissection is untreated. Patients with acute aortic dissection most commonly present with chest or back pain. Less frequently, it manifests without pain with predominant neurologic symptoms secondary to an acute stroke. We present the case of a 53-year-old male presenting with acute onset aphasia and right-sided weakness. Incidentally, CT angiography of his neck revealed a carotid artery dissection, which was found an extension of a Stanford type A acute aortic dissection resulting in a large vessel occlusion stroke. The patient's concomitant pathologies resulted in uncertainty as to the priority of management between the interventional neurology and cardiothoracic surgery services, ultimately resulting in the transfer of the patient to an aorta specialist at an outside facility. This case highlights several areas of difficulty in the management of patients with presenting with both large vessel occlusion stroke and acute aortic dissection and the need for consideration of acute aortic dissection in patients presenting with symptoms consistent with large vessel occlusion stroke. Optimal blood pressure control is unknown, as is the ideal timing of aortic repair and the potential for endovascular therapy for large vessel occlusion stroke in the setting of acute aortic dissection. Emergency physicians must rapidly engage with neurology, interventional neurology, and cardiothoracic surgery to determine appropriate interventions and timing of operative repair. The emergency physician must consider acute aortic dissection in patients presenting with signs and symptoms concerning for large vessel occlusion stroke, even if they have no complaint of chest pain, as administration of thrombolytics in these patients may be deadly.