Chronic cerebrospinal venous insufficiency (CCSVI) is a clinical picture, introduced in 2009, characterized by extracranial narrowing of the internal jugular vein (IJV). Not only the jugular variant of the Eagle syndrome but also intraluminal defects, external compressions, or venous hypoplasia could determine obstruction of the jugular venous blood flow; these conditions could present singularly or combined. For these reasons, in patients with complex vascular cases (Eagle jugular variant associated with other concomitant causes of IJV obstruction), the isolated classic styloidectomy could represent a significant failure as it cannot restore the flow in the IJV. In this chapter, we present two exemplificative complex vascular cases of multilevel IJV obstruction.