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Chronic internal carotid artery occlusion can be a difficult pathology to treat as the related recurrent transient ischemic attacks, hypoperfusion, and strokes lead to a progressive clinical decline even for patients on the best medical management. In this chapter, the role of medical management, endovascular intervention, and surgical bypass is discussed and the controversies that surround these management strategies are explored. The extracranial carotid–internal carotid (EC-IC) bypass is a technique that continues to be a point of contention in the chronic internal carotid artery occlusion treatment world. The debate of the usefulness of the EC-IC bypass derives from what is currently known in the literature and the dilemma of managing persistently symptomatic patients despite what is considered the standard optimal medical therapy. The assessment of patients with chronic internal carotid artery occlusion is discussed to help characterize the factors that impact clinical progression and may help identify a subset of patients who could potentially benefit from surgical intervention. This chapter offers an algorithm for assessing chronic internal carotid occlusion and delves into the utility of surgical and endovascular treatment strategies. The technique of the EC-IC bypass as well as common complications and their avoidance is described in detail. There is still much to be learned about the physiology of chronic carotid occlusion and the impact of fluid dynamic alterations on neurologic function preservation. Further understanding of this pathology may someday lead to a higher rate of success with treatment strategies.