Acute aortic syndrome (AAS) is classically attributed to three underlying pathologic conditions-aortic dissection (AD), intramural hematoma (IMH), and penetrating atherosclerotic ulcer (PAU). In the majority of cases, the basics of image interpretation are not difficult and have been extensively reviewed in the literature. In this article, the authors extend existing imaging overviews of AAS by highlighting additional factors related to the diagnosis, classification, and characterization of difficult AAS cases. It has been well documented that AAS is caused not only by an AD but by a spectrum of lesions that often have overlap in imaging features and are not clearly distinguishable. Specifically, phase of contrast enhancement, flow artifacts, and flapless AD equivalents can complicate diagnosis and are discussed. While the A/B dichotomy of the Stanford system is still used, the authors subsequently emphasize the Society for Vascular Surgery's new guidelines for the description of acute aortic pathologic conditions given the expanded use of endovascular techniques used in aortic repair. In the final section, atypical aortic rupture and pitfalls are described. As examples of pericardial and shared sheath rupture become more prevalent in the literature, it is important to recognize contrast material third-spacing and mediastinal blood as potential mimics. By understanding these factors related to difficult cases of AAS, the diagnostic radiologist will be able to accurately refine CT interpretation and thus provide information that is best suited to directing management. Online supplemental material is available for this article. ©RSNA, 2021.