The authors report a case of a 69-year-old man with a 5-year history of medically treated type B aortic dissection, who presented a new retrograde type A aortic dissection (RTAD) of the aortic arch and the ascending aorta. Clinical presentation was suggestive of pulmonary embolism. Computed tomographic angiography revealed a contained rupture of the dissected aortic arch, confined to the connective tissue plane between the arch and the pulmonary arteries. Extrinsic compression of both pulmonary arteries caused right heart failure. The patient was successfully operated with replacement of the dissected aortic arch, decompressing the pulmonary arteries. The combination of a secondary new RTAD after a chronic type B aortic dissection and a compression of the pulmonary arteries by a contained rupture of the dissected aortic arch have not been reported previously in literature.