The presentation, evaluation, management, and outcome of a case of type A circumferential dissection involving repeated retrograde intussusception of the intimal flap through the aortic valve is described in this case report. Fewer than 20 intimo-intimal intussusception cases have been described since the first report was published by Hufnagel in 1962, and outcomes have typically been poor because of delays in diagnosis. This case shows the potential for a positive outcome when the diagnosis of intimo-intimal intussusception is entertained and confirmed early in the course of treatment. Preoperative computed tomography and intraoperative transesophageal echocardiography were essential in diagnosis and operative planning.