Aortic dissection is an aggressive and life-threatening cardiac disease that’s highly challenging in surgical operation. Bentall procedure comes with potential complications. How to manage these complications is important when it comes to improving patient outcome. In this case, we present a 41-year-old male patient with iatrogenic aortic dissection. He had aortic valve replacement and repair of an atrial septal defect in 2012. After five years, he suffered reoperation for aortic dissection. A year later, the patient was readmitted for a voluminous pulsatile mass over the anterior thorax, confirming the presence of a huge pseudoaneurysm originating from the left coronary bottom performed during the Bentall procedure. This required a third operation to repair the hemorrhagic site. Pseudoaneurysm is a common complication after the inclusion technique in the Bentall procedure. Effective hemostasis or tension-free anastomosis is important toward improving patient outcome.