The evolution of surgical replacement of the aortic arch has been shaped by advances in surgical techniques and ancillary technologies. From the early pioneering attempts in the 1950s by Ho Ju Lin, Cooley, and DeBakey, which preceded the advent of cardiopulmonary bypass (CPB), the development of perfusion, cerebral protection, and surgical techniques, along with the evolution of prosthetic grafts, has progressively enabled surgeons to address these challenging conditions with greater confidence. Despite these remarkable advancements, aortic arch surgery still remains one of the most technically challenging procedures in cardiac surgery. A major turning point was the introduction of the elephant trunk technique by Borst in 1983. This approach allowed for staged treatment of diffuse aneurysmal disease, including both degenerative and post-dissection cases, and reduced the overall surgical risk across multiple procedures. Initially met with skepticism, the technique has since been universally adopted by centers specializing in aortic pathology. At the same time, numerous modifications to the technique have emerged. Each modification has addressed specific technical challenges or enabled the integration of new technologies. The development of the Siena graft in the early 2000s was driven by the need to harness the growing potential of endovascular devices, which had been evolving since the 1990s, and to address critical technical issues. These included the use of multi-branched prostheses and the introduction of an anastomotic collar to facilitate secure distal anastomoses, even in less-than-ideal anatomical conditions. The design of the Siena graft, now widely adopted by most manufacturers for arch grafts, required close collaboration with industry partners to ensure a reliable product from its inception. Today, the Siena graft remains a highly relevant platform for the treatment of diffuse aneurysmal disease that requires the elephant trunk technique. This paper describes the evolution and design of the graft, the technical approach, including pitfalls and safeguards, and our clinical experience.