A 21-year-old man with Marfan syndrome and known aortic root aneurysm presented to our emergency department with symptoms suggestive of acute aortic dissection. The patient was hemodynamically stable and bilateral upper extremity blood pressures were similar. There was no mediastinal widening on portable chest radiograph. Both contrast CT and retrograde angiography of the aorta failed to identify dissection. Subsequent transesophageal echocardiography demonstrated a Stanford classification type A dissection. This case demonstrates the utility of multiple imaging modalities for identifying aortic dissection in high-risk patients.