We present a novel endoscopic approach for the treatment of Zenker's diverticulum in anatomically challenging patients. Proper endoscopic exposure was not possible in these patients with Zenker's diverticulum and concomitant esophageal stricture without first addressing the esophageal stricture due to inability to properly seat the endoscopic stapler within the esophageal lumen. In each case, a two team approach was implemented. First, the gastroenterologist performed the esophageal dilatation then the otolaryngologist performed the endoscopic staple assisted diverticulostomy. Three patients were surgically treated for Zenker's diverticulum with esophageal dilatation followed by endoscopic staple assisted esophagodiverticulostomy from April 2005 to August 2009. All patients were women with ages ranging from 86 to 89 years. All patients had a preoperative barium esophagram. Preoperative symptoms included dysphagia, aspiration, and regurgitation. There were no immediate postoperative complications related to the procedure. All patients resumed an oral diet within the first 24 hours after surgery and were discharged home on postoperative day one. The results of this study suggest that esophageal dilatation followed by ESED is a safe and effective method of surgically correcting Zenker's diverticulum with concomitant esophageal stricture. This study suggests that those patients who previously were not endoscopic treatment candidates due to inability to engage the endoscopic stapler may now be candidates for endoscopic treatment. Since this procedure involves the intervention of both an otolaryngologist and gastroenterologist, appropriate counseling before the procedure is important. Additionally, the potential need for an open approach should be discussed preoperatively. Further studies with longer periods of follow-up are warranted to evaluate the long term complications, relapse rate and cost efficacy of this approach.