We describe a case of hybrid total thoracic aortic repair and valve-in-valve transcatheter aortic valve replacement in a high-risk patient with complicated chronic type A dissection and severe prosthetic aortic stenosis. The patient underwent a three-stage-procedure including aortic arch debranching, thoracic endovascular aortic repair of the ascending aorta, aortic arch and descending thoracic aorta, and direct aortic valve-in-valve replacement using transcatheter heart valve. The details of the procedures are described with a discussion of the challenges and the decision-making process.