Background: Iatrogenic type A dissections can be managed conservatively, but clear guidelines for treatment are lacking. Case presentation: This case illustrates a borderline situation that necessitated a change in treatment approach. A patient underwent endo-prosthetic treatment for an aneurysm. During the insertion of a guiding catheter through the axillary artery, the ascending aorta was dissected, with contrast injected into the vascular wall. Due to the mechanism of injury and the absence of an intra-aortic intimal tear (as evidenced by contrast stagnation in the false lumen), conservative management was initially chosen. A follow-up computed tomography (CT) scan showed complete resolution after 1 month. However, 10 days later, the patient was readmitted with acute chest pain, and a new CT scan revealed an acute dissection, with a free-moving intimal flap in the ascending aorta, requiring emergency surgery. Current guidelines recommend surgery for iatrogenic type A dissections that extend or propagate several centimeters into the ascending aorta. However, these guidelines do not account for the mechanism of injury, the localization, or the size of the intimal tear. Conclusion: In this case, the assumption of spontaneous healing with an intact intima was initially supported. However, further developments highlight the importance of clinical and radiological follow-up, regardless of the injury’s mechanism. Relevance for patients: Iatrogenic aortic dissection is a highly complex condition that requires close monitoring and, if necessary, a reassessment of the chosen treatment strategy.