A 71-year-old woman presented with acute chest pain and was admitted at our institution. Computed tomography revealed a penetrating atherosclerotic ulcer in the ascending aorta with extensive intramural hematoma. A transapical endovascular stenting was successfully performed. Computed tomography at a 6-month follow-up visit revealed a type I endoleak, which was restented through the same approach. Despite initial satisfactory results, follow-up revealed a persistent endoleak, so that a high-risk open surgical repair was required. Surgical replacement of the ascending aorta was successfully performed without postoperative neurologic deficit.