Background The purpose of our study was to examine when and how to implement the current endoluminal stent graft technology to treat ascending aortic disease. Methods During a 7-year period (March 2006 through July 2013), 7 consecutive patients (median age, 69 years; range, 61.5 to 80.5 years) with multiple comorbidities underwent endoluminal repair of the ascending aorta. Six had an ascending aortic pseudoaneurysm, and 1 had iatrogenic coarctation. The median number of prior sternotomies was 2 (range, 1 to 4). Results Technical success was achieved in all but 1 patient, with 1 death (14.3%) at 30 days. The endoluminal technology used included the Gore TAG (W.L. Gore and Associates, Flagstaff, AZ) thoracic graft (including the new C-TAG) in 6 patients, the Talent stent graft (Medtronic, Santa Rosa, CA) in 1, an Excluder cuff (W.L. Gore) in 2, and an Amplatzer occluder (AGA Medical Corp, Plymouth, MN) in 1. More than 1 stent was placed in 4 patients. Three patients required innominate artery stenting, and 1 required additional left common carotid artery stenting. One patient (14.3%) required intraoperative conversion to open surgical repair. Median follow-up was 14.4 months (interquartile 25th to 75th percentile range, 5.5 to 22.6 months) with 66.6% overall survival. No aortic-related death was reported during the follow-up period. Conclusions Stent grafting of the ascending aorta is feasible but limited and is reserved for high-risk individuals. Technical expertise is essential, and follow-up is mandatory. Technical points, tips, and challenges of the current endovascular technology to effectively treat the ascending aorta are described.