Two case reports demonstrate the paradoxical occurrence of achalasia many years after the successful surgical treatment of gastroesophageal reflux disease (GERD). These patients had remedial surgery laparoscopically. The three types of achalasia syndromes that can follow antireflux surgery are discussed. In type 1, primary achalasia is misdiagnosed as GERD and inappropriate antireflux surgery causes worsening dysphagia immediately after surgery without any symptom-free interval. In type 2, secondary iatrogenic achalasia is seen early after antireflux surgery and is characterized by the presence of stenosis and scar formation at the site of the fundic wrap. Although the motility studies resemble achalasia, the repair needs only to be taken down and refashioned when there is no response to balloon dilatation. In type 3, illustrated by the case reports, primary achalasia follows antireflux surgery after a significant symptom-free interval. There is complete absence of any stenosis or fibrosis of the esophagus and periesophageal tissues at remedial surgery. Moreover, surgical treatment of this condition needs to include esophageal myotomy.