All patients surviving an acute aortic dissection require continued lifelong surveillance of their diseased aorta. Late complications, driven predominantly by chronic false lumen degeneration and aneurysm formation, often require surgical, endovascular, or hybrid interventions to treat or prevent aortic rupture. Imaging plays a central role in the medical decision-making of patients with chronic aortic dissection. Accurate aortic diameter measurements and rigorous, systematic documentation of diameter changes over time with different imaging equipment and modalities pose a range of practical challenges in these complex patients. Currently, no guidelines or recommendations for imaging surveillance in patients with chronic aortic dissection exist. In this document, we present state-of-the-art imaging and measurement techniques for patients with chronic aortic dissection and clarify the need for standardized measurements and reporting for lifelong surveillance. We also examine the emerging role of imaging and computer simulations to predict aortic false lumen degeneration, remodeling, and biomechanical failure from morphological and hemodynamic features. These insights may improve risk stratification, individualize contemporary treatment options, and potentially aid in the conception of novel treatment strategies in the future.