Background The authors present two cases with type B aortic dissection initially treated by endovascular stent graft who developed aortic complications posttreatment and required surgical treatment. Case Description A 50-year-old woman and a 65-year-old man underwent endovascular treatment for thoracic aortic aneurysm associated with type B dissection and -both of them evolved with endoleak type 1. The first case was related to aortobronchial fistula, and the second one was associated with ascending aortic aneurysm. An extra-anatomical ascending aorta-supraceliac aorta bypass grafting was decided due to the persistent leak. Conclusion Surgery is an excellent choice for complex complications after thoracic endovascular aortic repair with previous failed attempts of endovascular resolution.