A 40-year-old man presented with a major nondominant hemisphere stroke syndrome after a road traffic accident. Cranial computed tomography scan revealed an extensive right hemisphere infarction involving the entire anterior and middle cerebral artery territories. Duplex Doppler ultrasound and cerebral angiography revealed bilateral internal carotid artery dissection with evidence of underlying fibromuscular dysplasia. Anticoagulation with heparin was commenced despite the coexisting large cerebral infarction, with the objective of protecting the uninjured but at-risk left cerebral hemisphere from ischemic injury. Patients with multiple cerebral arterial dissections complicated by cerebral infarction present a significant management dilemma. Our literature review revealed a lack of clear management guidelines for such cases.