Purpose The surgical intervention for ascending aortic pathologies has seen a marked evolution over the years, due to the intertwined combination of technological improvements in equipment, as well as s a better understanding of its natural history. Anecdotal evidence at our centre has demonstrated a potentially increased stroke rate amongst patients who underwent complex ascending aortic endovascular surgery. The objective of this project is to identify risk factors based on available preoperative and intraoperative clinical data which best predict post-operative stroke rates amongst these patients. Methodology Deriving data from the Alfred aortic database, an observational study was conducted using a prospectively-maintained institutional dataset to identify patients who underwent aortic endovascular surgery involving either the ascending aorta and/or aortic arch. Following this, pre-operative patient characteristics, types of stents used, size and route of access sheaths and coverage were evaluated for all patients who underwent endovascular ascending/arch intervention between January 2020 to June 2025. Strokes were defined as radiological (either CT or MRI) evidence of infarcts on cross-sectional neuroimaging. Results We identified 118 ascending aortic and arch endovascular cases over a 5-year period, all of which were included in this study. The overall stroke rate was 5.1%. Independent predictors of strokes included subclavian to carotid transposition (OR 5.2, p-value 0.30), a Type II/III aortic arch (OR 10.1; p-value 0.54) and presence of aortic atheroma (OR 3.1, p-value 0.04). Conclusion In our retrospective single-centre experience, ascending aortic and arch endovascular procedures were associated with a 5.1% stroke rate, with factors associated with stroke development including carotid transposition surgery to facilitate stent deployment, aortic arch anatomic anomalies and the presence of aortic atheroma.