Background: A 64-year-old woman presented with dilatation of the distal aortic arch secondary to chronic type B aortic dissection. Case Report: The patient underwent fenestrated thoracic endovascular aortic repair (TEVAR) for closure of the entry site, and reconstruction of the left subclavian artery with a covered stent. On the 40th postoperative day, a retrograde type A aortic dissection (RTAD) was observed on computed tomography and she underwent emergency surgery. The entry tear, related to the proximal bare metal stent, was located in front of the aortic arch. A partial aortic arch replacement was performed. Conclusion: Consideration of the risk factors of RTAD is important when performing TEVAR.