Intramural esophageal dissection (IED) is an uncommon disorder characterized by separation of the mucosal and submucosal layers of the esophagus. Iatrogenic intervention is the most common cause of IED, but spontaneous dissection is rare. We report an unusually complicated case of spontaneous IED that involved the full-length of the esophagus that necessitated surgical intervention due to infection of the false lumen. In this case, chest computed tomography successfully established the diagnosis and aided in pre-operative evaluation with the use of various image post-processing techniques.