We present a case of a 7-year-old boy with a distal esophageal stricture in the setting of severe gastroesophageal reflux disease that dated to infancy and a sliding paraesophageal hernia. He had been lost to follow-up prior to presenting to our Pediatric Gastroenterology service with dysphagia and failure to thrive. Medical and endoscopic management of his reflux and stricture were unsuccessful and he was referred to our clinic for operative management. We proceeded with a laparoscopic paraesophageal hernia repair but after distal esophageal mobilization, we were unable to obtain adequate intraabdominal esophageal length for an effective repair and fundoplication. Therefore, esophageal lengthening was performed via a stapled Collis gastroplasty. A 3-centimeter Nissen fundoplication was performed, followed by a gastrostomy tube placement for enteral access, given his weight loss. The patient recovered well and is slowly regaining his weight. An esophagram at six months revealed resolution of his stricture.