The introduction of transcatheter aortic valve replacement (TAVR) has undeniably changed the landscape of valvular heart disease management over the last two decades. A reduction in complications through improvements in techniques, experience, and technology has established TAVR as a safe and effective alternative to surgical aortic valve replacement. However, it is important to consider the potential risks associated with TAVR and ways in which life-threatening complications can be identified and managed in a timely fashion. In this article, we review some catastrophic iatrogenic aortic injuries that are described in the literature and present a case of an acute iatrogenic type A aortic dissection that occurred during a transcatheter aortic valve replacement (TAVR). After valve deployment, a routine neurologic examination noted the new onset of a left-sided facial droop and upper extremity weakness. Urgent imaging revealed an extensive type A aortic dissection, and the patient was taken to the operating room for surgical repair. The coordination of our multidisciplinary team allowed for prompt recognition of her neurologic symptoms, urgent imaging, and timely transport to the operating room, all of which contributed to the successful management of this life-threatening procedural complication.