The ascending aorta, with its hostile angulations and forces, is the next frontier in the evolution of endovascular surgery. Type II hybrid arch repair, involving surgical replacement of the ascending aorta, arch debranching, and stent graft deployment in the ascending aortic graft, offers an opportunity to study the behavior of an endovascular prosthesis in the ascending aorta. We report complications seen at the proximal landing zone after type II hybrid arch repair. A dedicated imaging protocol was used to monitor 20 consecutive patients who underwent type II hybrid arch repair at a single center from June 2009 to July2014. Mean age was 66 years (range, 47 to 82 years). Mean imaging follow-up was 34 months (range, 12 to 64 months). There was 1 operative death (5%). Bird beaking (>5 mm of nonapposition) of the stent graft at the proximal landing zone occurred in 12 patients, and >20 mm of bird beaking occurred in 7 patients. Proximal landing zone complications occurred in 4 patients (20%), comprising 2 type Ia endoleaks, 1 graft migration, and 1 graft infolding detected on postoperative days 4, 11, 5, and 755, respectively. Three patients underwent endovascular reintervention for proximal landing zone complications. There were no late deaths. Thoracic aortic stent grafts may be prone to proximal landing zone complications when deployed in the ascending aorta. Bird beaking is common when endografts are deployed in the Dacron (DuPont, Wilmington, DE) ascending aorta. Angulation issues will likely need to be overcome by stent graft refinement to enable future closed chest approaches to the ascending aorta.