Background-Optimal management strategy of acute aortic dissection (AD) with retrograde extension from entry tear in the descending aorta into the ascending aorta remains undetermined. Methods and Results-Of the 538 patients who were diagnosed as having acute AD from 1999 through 2011, 49 patients (37 men; 52.5±13.1 years) were identified as having entry tear in the descending aorta with retrograde extension of AD into the ascending aorta. Sixteen patients who were clinically stable with thrombosed false lumen in the ascending aorta were treated medically (MED group), whereas 33 patients underwent aortic replacement (SURG group) on an intentionto-treat basis. In the MED group, 1 patient was converted to urgent aortic surgery and 2 patients underwent endovascular stent grafting in the descending aorta during the initial hospitalization. The early (30-day or in-hospital) mortality rates were 0% and 9.1% in the MED and SURG group, respectively (P=0.54).