Treatment of thoracic aortic dissection remains highly challenging and is rapidly evolving. Common classifications of thoracic aortic dissection include the Stanford classification (types A and B) and the DeBakey classification (types I to III), as well as a new supplementary classification geared toward endovascular decision making. By using various imaging techniques, the extent of the dissection, the location of the primary intimal tear, the shape of the aortic arch, and the zonal involvement of the aortic arch-factors that affect the treatment strategy-can easily be identified. Thoracic endovascular aortic repair (TEVAR) is generally performed in two groups of patients: (a) those with a surgically repaired type A dissection, and (b) those with a complicated type B dissection. Several imaging findings can help predict the course of remodeling of the dissected aorta after a repaired type A dissection and TEVAR. A spectrum of imaging findings exist with regard to favorable (positive) or failing (negative) remodeling. A schematic model with imaging support allows the classification of important causes of failing remodeling into proximal and distal groups, on the basis of the origin of the refilling of the false lumen and the underlying pathophysiology of pressurization. Refilling of the false lumen of the aorta after repair of a type A dissection is usually secondary to a persistent intimal tear at the aortic arch, a leak of the distal graft anastomosis, or refilling from the false lumen of a dissected aortic arch vessel. After TEVAR, false lumen refilling is most commonly due to an incomplete seal of the proximal landing related to the aortic tortuosity, an arch branch stump, a supra-arch chimney stent, or the TEVAR technique. Online supplemental material is available for this article. ©RSNA, 2018.