Thoracic endovascular aortic repair (TEVAR) has become the standard of care for descending thoracic aortic pathology as the procedure has a historically low rate of reintervention and a high rate of success. However, TEVAR can be associated with complications such as endoleak, upper extremity limb ischemia, cerebrovascular ischemia, spinal cord ischemia, and post-implantation syndrome.An 80-year-old man with a history of complex thoracic aortic aneurysms underwent repair of a large thoracic aneurysm with a frozen elephant trunk procedure in 2019 at an outside institution. The proximal aortic graft extended to the arch and the innominate and left carotid artery were implanted into the distal portion of the graft. The endograft, extending from the proximal graft to the descending thoracic aorta, was fenestrated to maintain left subclavian artery flow. In an attempt to gain a seal at the fenestration, a Viabahn graft (Gore, Flagstaff, AZ, USA) was inserted. A type III endoleak was identified postoperatively at the fenestration, and a second Viabahn graft was required to gain a seal during the initial hospitalization. In 2020, an endoleak persisted at the fenestration on follow-up imaging, but the aneurysmal sac was stable. No intervention was recommended. The patient later presented to our institution with three days of chest pain. A type III endoleak at the level of the subclavian fenestration persisted with significant enlargement of the aneurysm sac. The patient underwent an urgent repair of the endoleak. This consisted of covering the fenestration with an endograft and left carotid to subclavian bypass. Subsequently, the patient developed a transient ischemic attack (TIA) due to kinking and extrinsic compression by the large aneurysm sac of the proximal left common carotid artery, requiring a right carotid to left carotid-axillary graft bypass.This report with a literature review discusses TEVAR complications and outlines methods to approach them. TEVAR complications and their management should be firmly understood to improve overall treatment outcomes.