We describe a 64-year-old man with squamous cell carcinoma of the esophagus who presented with an obstruction of the esophagus following radiation therapy and chemotherapy. Initial upper gastrointestinal barium swallow studies showed a complete stoppage of the barium column, not unlike that of a congenital esophageal atresia. Therapeutic endoscopy was performed using a two-endoscope, two-operator system that reestablished patency of the esophagus. Repeated endoscopy was then used to continue esophageal dilation with eventual placement of a permanent stent. A video and a comprehensive review of the literature regarding combined antegrade-retrograde dilation techniques used to date are also provided.