Benign anastomotic strictures occur frequently after esophagectomy, and impact on postoperative recovery, nutritional status, and quality of life. This large cohort study explored the incidence of stricture after transthoracic (2- and 3-stage) and transhiatal resections with uniform single-layer sutured anastomotic technique, and aimed to identify independent risk factors. Patients undergoing esophagectomy with gastric conduit reconstruction between February 2001 and October 2014 were studied prospectively. Symptomatic anastomotic stricture was defined as dysphagia requiring endoscopic dilatation, and refractory strictures as those requiring >5 dilatations. Multivariable logistic regression was performed to determine factors independently associated with stricture development. Five-hundred and twenty-four patients, 77% with adenocarcinoma, underwent esophagectomy [2-stage, n=328 (62.6%); 3-stage, n=129 (23.3%); transhiatal, n=74 (14.1%)], with an overall inhospital mortality rate of 2.7%. 58.5% of patients received neoadjuvant therapy [chemotherapy only, n=119 (22.7%); chemoradiation, n=188 (35.9%)]. Anastomotic stricture developed in 125 patients (24.5%), was refractory in 20 (3.9%) and required a median of 2 dilatations (range 1-18). On multivariable analysis, ASA grade (P<0.05), cervical anastomosis (P<0.001), and a significant postoperative cardiac event (P<0.05) were independently associated with stricture risk. Refractory strictures were independently associated with anastomotic leak (P=0.01) and transhiatal resections (P<0.001). Benign anastomotic strictures are common, particularly with cervical reconstruction, and after transhiatal resection. Refractory strictures are rare. Where fitness and oncologic equivalence apply, a thoracic anastomosis provides significant advantages compared with a cervical anastomosis in terms of anastomotic stricture risk.