Abstract Background Anastomotic stricture is a recognised complication after oesophagectomy. It can impact the patient’s quality of life and may require recurrent dilatations. The aim of this study was to evaluate the frequency of benign strictures, contributing factors, and the long-term outcomes of management in patients undergoing oesophagectomy with thoracic anastomosis using a standardised circular stapler technique. Methods All patients who underwent a two-stage transthoracic oesophagectomy with curative intent between January 2010 and December 2019 at this single, high volume centre were included. All patients who underwent a stapled (circular) intrathoracic anastomosis using gastric conduits were included. Those with variations to anastomotic technique or those not having a transthoracic anastomosis were excluded to reduce heterogeneity. Patients who developed malignant anastomotic strictures and patients who died in hospital were excluded from the analysis. Benign stricture incidence, number of dilatations to resolve strictures, and refractory stricture rate were recorded and analysed. Results Overall, 705 patients were included with 192 (27.2%) developing benign strictures. Refractory strictures occurred in 38 patients (5.4%). One, two, and three dilatations were needed for resolution of symptoms in 46 (37.4%), 23 (18.7%), and 20 (16.3%) patients respectively. Multivariable analysis identified the occurrence of an anastomotic leak (OR 1.906, 95% CI 1.088-3.341, p = 0.024) and circular stapler size <28mm (OR 1.462, 95% CI 1.033-2.070, p = 0.032) as independent predictors of stricture occurrence. Patients with anastomotic leaks were more likely to develop refractory strictures (13.1% vs. 4.7%, OR 3.089, 95% CI 1.349-7.077, p = 0.008). Conclusions This study highlights that nearly 30% of patients having a circular stapled anastomosis will require dilatation after surgery for a benign anastomotic stricture. Although the majority will completely resolve after 2 dilatations, 5% will have longer-term problems with refractory strictures. Smaller circular stapler size and anastomotic leak have been identified as independent risk factors for developing a benign anastomotic stricture following oesophagectomy, and these patients should be monitored closely for symptomatology following surgery.