The aim of this study was to report the incidence, risk factors, and management of gastric conduit dysfunction after esophagectomy in 177 patients over a 3-year period in a single center. Patients with anastomotic strictures or delayed gastric emptying (DGE) were identified from a prospective database. Anastomotic strictures occurred in 48 patients (27%). Eighty-three percent of early anastomotic strictures (<1 year) were benign, and all late strictures (>1 year) were malignant. Dilatation was effective in 98% of benign and 64% of malignant strictures. DGE occurred in 21 patients (12%), and was associated with both anastomotic leak (P = 0.001) and anastomotic stricture (P = 0.001). 4/8 patients with late DGE (>3 months postesophagectomy) were tumor-related. Pyloric dilatation was effective in 92% of early and 63% of late DGE. Pyloric stents were inserted in 3 patients with tumor-related DGE. After esophagectomy, early anastomotic strictures (within 1 year) and early delayed gastric emptying (within 3 months) are usually benign and respond to dilatation. However, patients presenting later with tumor-related obstruction are unlikely to respond to anastomotic or pyloric dilatation and should be stented.