We present what is believed to be the first reported case of recurrent esophageal dissection in a previously healthy 33-year-old man with chronic eosinophilic esophagitis. He had two episodes of spontaneous dissection of the midesophagus separated by a 5-month interval. Both episodes responded to treatment with endoscopic intervention. He has remained free of additional recurrences after definitive endoscopic therapy and oral steroid therapy. A complete description of the case, relevant radiologic imaging, and a review of the relevant literature are provided.