The development of a ureteroenteric anastomotic (UEA) stricture has been reported in up to 15% of patients undergoing radical cystectomy (RC) with urinary diversion. Although benign strictures are thought to be the result of ischemia, the incidence, risk factors, and outcomes of patients with malignant UEA strictures have not been well described. We reviewed 2,523 patients treated with RC for bladder cancer from 1980 to 2012 at Mayo Clinic. Patients diagnosed with a UEA stricture following the surgery were identified, and a subset with malignant UEA was then analyzed. Cox proportional hazard regression models were performed to evaluate factors associated with the diagnosis of malignant UEA. Survival was assessed using the Kaplan-Meier method. At a median of 10.5 years of follow-up, 232 (9.2%) patients were diagnosed with UEA stricture, of which 38 (16.4%) had malignant strictures (MS). Median time from RC to the diagnosis of a malignant vs. benign UEA stricture was 32.4 months and 7.2 months, respectively (P = 0.004). Pathologic non-muscle-invasive disease stage at RC was more common among patients diagnosed with a MS compared with patients who did not develop a MS (71.1% vs. 45.9%; P = 0.002). The presence of carcinoma in situ on initial ureteral margin at RC was associated with a significantly increased risk of subsequent diagnosis (hazard ratio = 4.1; P<0.001). Following malignant stricture diagnosis, 2- and 5-year cancer-specific survival was 50% and 30%, respectively, whereas overall survival was 44% and 23%, respectively. MS are uncommon after RC, and present later than benign strictures. Ureteral margin involvement with carcinoma in situ was associated with a significantly increased risk of MS diagnosis.