Chronic type B aortic dissection (cTBAD) is a rare but challenging condition that requires individual treatment strategies. Especially the long-term therapy impacts prognosis. In this single-center retrospective study, we evaluated patients with cTBAD in our vascular outpatient clinic over 10 years. Follow-up consultations included contrast-enhanced, electrocardiogram-triggered, high-resolution CT angiography (CTA) covering the entire aorta. Evaluated characteristics went beyond demographic characteristics combining the treatment approach and the timing and occurrence of potential complications. We analyzed 133 patients in total (n = 92, 69.2% male) with cTBAD with a mean follow-up of 67.7 months. Most of them underwent invasive treatment (n = 102, 76.7%), the majority received thoracic endovascular aortic repair (TEVAR) (n = 82, 61.7%). A total of 80 patients (60.2%) had major complications, whereas over a third was free of complications even after 5 years. Most common complications were progress of dissection and endoleaks, aneurysms of true (TL) and false lumen (FL) were more common in the later time periods. The treatment of cTBAD in terms of timing, therapy approach, and complications is still challenging for the entire aortic team. Nevertheless, the early recognition of complications permits promising treatment options and highlights the importance of frequent follow-up examinations especially within the first years.