This study highlights the prevalence and conservative management strategies of iatrogenic ascending aortic dissection after percutaneous intervention (PCI) of chronic total occlusion (CTO). Retrospective analysis on patients who underwent CTO PCI from one medical center from 2020 to 2022 was performed by two operators. Data was obtained from the Prospective Global Registry for the Study of CTO database. Out of 318 patients, there were six reported cases of iatrogenic ascending aortic dissection. The causes of dissection included guiding catheter trauma, antegrade injection, two retrograde injection, and two cases of balloon rupture after lithotripsy. IVUS-guided stenting of the coronary back to the origin to seal the entry of the dissection flap occurred in two patients. All patients had a conservative management approach. No patient had to undergo urgent surgery. While the incidence remains rare, complications, including aortic dissection, are more frequent in CTO PCI as compared to non-CTO PCI. IVUS can be used to complete coronary intervention so long as the patient remains clinically and hemodynamically stable. Patients should have formal imaging with either transesophageal echocardiogram or computed tomography angiography. The outcomes of patients who experience iatrogenic aortic dissection during CTO PCI with stable coronary disease seem to be better than in patients with acute coronary syndrome.