Intramural esophageal dissection (IED) is a rare clinical entity involving a mucosal injury and creation of a true and false lumen within the esophagus. We report on a case of IED caused by repeated vomiting due to a small bowel obstruction associated with a small amount of pneumomediastinum on CT. IED has traditionally been believed not to be associated with esophageal perforation. Our case adds to the few reported instances where IED has been associated with extraluminal air leakage, the mildest form of esophageal perforation and demonstrates imaging not previously published in the radiology literature. Our case was successfully managed conservatively.