Retrograde gastroesophageal intussusception has been rarely reported in the literature. Risk factors include poor fixation of the stomach due to either long or loose mesenteric attachments; high intraabdominal pressure due to retching, physical exertion, or ascites; and hiatal hernia, which can lead to the development of a large gastroesophageal opening. An attempt at endoscopic reduction is reasonable, but laparotomy and manual reduction is usually required. We report a case of retrograde gastroesophageal intussusception in a patient with long-standing achalasia and two previous Heller myotomies.