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Background: Anastomotic leak is one of the most feared complications of esophagectomy. Previous studies have suggested a potential link between aortic calcifications detected on routine preoperative CT scans and increased risk of anastomotic leak after esophagectomy. This study aims to investigate whether clinicians' assessment of aortic calcifications can predict the occurrence of anastomotic leaks in patients undergoing esophagectomy for cancer. Methods: A long‐term follow‐up was conducted on consecutive patients with esophageal cancer who underwent elective open esophagectomy at a Finnish tertiary hospital. Aortic calcifications were evaluated based on CT scans and categorized on a 0–3 scale reflecting the number of calcifications in the affected segment of the aorta. Reviewers assessing the calcifications were blinded to clinical details and postoperative outcomes. Results: The study included 97 patients (median age: 64 years and range: 43–78; 20% female), with a median follow‐up time of 1307 (2–1540) days. Among them, 22 patients (23%) had postoperative anastomotic leak. We observed a significant association between calcifications in the descending aorta and a higher risk of anastomotic leak (p = 0.007), as well as an earlier occurrence of leak postoperatively (p = 0.013). However, there was no association between aortic calcifications and increased mortality. Conclusions: Presence of calcifications in the descending aorta is independently associated with an increased risk of anastomotic leaks following esophagectomy for cancer. Identifying patients at higher risk for this complication could facilitate appropriate pre‐ and postoperative interventions, as well as enable earlier diagnosis and treatment to mitigate the severity of the complication. [ABSTRACT FROM AUTHOR]