We report a case of ruptured chronic type B aortic dissecting aneurysm that was successfully treated with the Candy plug technique to exclude a false lumen. A 57-year-old man had undergone abdominal fenestration for complicated acute type B aortic dissection previously. He then underwent debranching TEVAR for an impending rupture because of a dilated thoracic aortic dissecting aneurysm in 2014. After one year, the aneurysm was ruptured because of continuous distal flow of the false lumen. We performed TEVAR using the Candy plug technique, and he was discharged on the 11th postoperative day. The false lumen diameter was reduced. TEVAR using the Candy plug technique for chronic type B aortic dissection was thought to be useful in high-risk patients, but we need more careful observation.