The development of thoracic endovascular aortic repair in recent years has revolutionised the way aortic disease is treated. However, there are potential complications associated with this which can be life threatening and pose a difficult challenge to manage. We present a case of retrograde ascending aortic dissection complicating thoracic endovascular aortic repair, and its repair using a technique of continuous perfusion “branch-first” aortic arch replacement. We discuss the complication of retrograde ascending aortic dissection and the issues that affect its surgical management.