Penetrating atherosclerotic ulceration of the aorta is a poorly understood entity that clinically mimics classic aortic dissection but has imaging features that are distinctly different. In a review of 16 patients with penetrating atherosclerotic ulceration, patients were typically hypertensive (n = 14), and they experienced chest or back pain (n = 13). All patients had an abnormal chest radiograph, with diffuse (n = 14) or focal (n = 2) enlargement of the descending thoracic aorta. Features at contrast material-enhanced computed tomography (CT) included intramural hematoma (n = 16), focal ulcer (n = 15), displaced intimal calcification (n = 13), pleural and/or extrapleural fluid (n = 7), mediastinal fluid (n = 4), and a thick or enhancing aortic wall (n = 6). The chest radiograph and CT findings were compared in patients treated conservatively (n = 9) and surgically (n = 7). These findings did not correlate with the need for surgery. Eight of nine conservatively treated patients were asymptomatic after treatment with antihypertensive medication. Contiguous dynamic contrast-enhanced CT of the aorta enables distinction of ulceration from dissection, which is particularly important in the hemodynamically unstable patient because the surgical management of ulceration is more extensive than that for aortic dissection.