Delayed ascending aortic dissection following coronary artery bypass surgery is a rare but lethal complication. We present the case of a 54-year-old man with a delayed acute Stanford A aortic dissection following an off-pump coronary artery bypass surgery in preexisting chronic type B disease. Such a case of an iatrogenic acute aortic dissection poses a significant challenge and dilemma in choosing the best technique for coronary revascularization in this group of patients. The pathophysiology and technical options are discussed.