Complete esophageal obstruction is a challenging problem that is not amendable to standard dilation techniques. Multiple endoscopic techniques as well as radical surgical procedures have been developed with the goal of restoring a patent esophageal lumen. In patients with complete esophageal obstruction, an antegrade-retrograde technique has been described, but this generally depends on the ability to transilluminate across the stricture. Successful transillumination allows for safe direct puncture across the stricture, followed by dilation. In long-segment strictures (greater than 2-3 cm), transillumination may not be possible. We report a case of a 63 year-old woman who developed a complete esophageal obstruction from radiation therapy (RT) for hypopharyngeal squamous cell carcinoma. She did have enteral access via a percutaneous endoscopic gastrostomy (PEG) tube which had been placed prior to beginning RT. A combined antegrade (through the mouth) and retrograde (through PEG site) approach was done, but transillumination across the stricture failed. Fluoroscopy demonstrated a 4 cm long stricture. The creation of a submucosal tunnel from the retrograde direction decreased the stricture length to 15 mm and transillumination was achieved. This allowed safe puncture of the stricture, placement of a guidewire, then successful dilation. The patient can now tolerate soft foods and maintain her weight. Submucosal tunneling can be used to achieve transillumination for the combined antegrade-retrograde approach to complete esophageal obstruction.