Percutaneous balloon dilation with or without placement of an external biliary drain is a nonoperative alternative method for treating benign bilioenteric anastomotic strictures. Although this procedure has a high technical success rate, outcomes are less optimal when attempting to dilate refractory tight strictures. For the stricture, cutting balloon can be an option. We present four patients with benign bilioenteric anastomotic strictures refractory to conventional balloon dilation. To the patients, a peripheral cutting balloon over-the-wire system was inflated, following subsequent conventional non-compliant balloon dilation. After the balloon dilation treatment, an external drainage catheter was placed through the stricture site and maintained for up to 30 days. Technical and end-treatment success was achieved in all four patients. In conclusion, the use of cutting balloon dilation may appear to be a safe and effective alternative method of treatment in patients with benign bilioenteric anastomotic strictures refractory to conventional balloon dilation.