The treatment of complex aortic pathology involving both the ascending and descending aortic segments at the same time represents a surgical challenge, with high postoperative morbidity and mortality rates reported. Over the past 27 years, different open surgical and endovascular techniques have been introduced and applied in various two-stage- or one-stage approaches to such cases. Thus, in 1983, Hans Borst significantly changed the traditional two-stage approach by introducing his elephant trunk technique. Leaving a segment of Dacron prosthesis reaching into the descending aorta during the first stage, the second-stage replacement of the residual dilated descending aorta was made far easier. The presence of interval mortality between the two stages, the unaffected need for two large operations to complete aortic repair, and the general failure of some patients to return for the second-stage repair set the scene for the development of one-stage procedures, both open surgical or hybrid surgical and endovascular, such as the frozen elephant trunk. However, the size of the operation, on the one hand, and the risk of spinal cord injury and need for surgical or endovascular completion during follow-up, on the other, have dampened enthusiasm. Recently, the introduction of supra-aortic debranching and endovascular aortic arch stent-graft repair has yet extended treatment to high-risk patients unsuitable to the more aggressive surgery, but mid- and long-term follow-up results are lacking. The lack of randomization and the presence of procedural and complication-related limitations for each technique do not allow for definitive conclusions about the ideal procedure to treat complex aortic pathology. However, the technical revolution experienced over the past 27 years, along with the improvement in perioperative management, has produced outstanding morbidity and mortality results even in this challenging patient population, but the decision regarding which pathology correlates with what operation remains highly debated and dependent also on regional competence.