Sleeve gastrectomy (SG) is the most frequently performed operation for morbid obesity in the world. In spite of its demonstrated efficacy, the Achilles’ Heel of this procedure seems to be either pre-existing or de novo gastro-esophageal reflux disease (GERD) with its potential complications such as peptic esophagitis, Barrett's esophagus and, in the long-term, esophageal adenocarcinoma. According to factual literature, it appears clear that Roux-en-Y gastric bypass is the preferred choice in case of pre-existing GERD or hiatal hernia discovered during preoperative workup for bariatric surgery. Nonetheless, certain authors propose performance of SG with an associated antireflux procedure such as Nissen fundoplication. Strict endoscopic surveillance is recommended after bariatric surgery. Revisional surgery (conversion of SG into Roux-en-Y gastric bypass (RYGB)) is the treatment of choice for patients who develop GERD after SG when conservative treatment (modified lifestyle and proton pump inhibitors) has failed. Lastly, with regard to the risk of esophageal adenocarcinoma after SG, large scale studies with adequate follow-up are necessary to come to factual conclusions. In all cases, the management of this conundrum remains a major technical challenge that has to be taken in consideration in future years, especially because of the current expansion of bariatric surgery.