Penetrating ulcer of the aorta has been recognized as a distinct aortic disorder, defined by the ulceration of an atherosclerotic plaque. The lesion has the potential to evolve acutely into aortic rupture, but chronic pictures are possible. Late evolution into rupture, frank aortic dissection and progressive aortic enlargement have been documented. We discuss different modalities of presentation on the basis of recent clinical cases. As the optimal treatment, either surgical (open or endovascular) or medical, is based on a correct diagnosis, we highlight the importance of including aortic ulcers in the differential diagnosis of chest pain. Although endovascular treatment can be advisable in cases with favorable anatomic condition and in patients with multiple comorbidities, the open surgical option should be available given the heterogeneous location and clinical scenarios of these lesions.