An 8 month old castrated male domestic shortthair was presented for evaluation of hyporexia, lethargy, and vomiting within five minutes of eating. The patient had initially been seen the month prior for an abdominal exploratory surgery following a three day history of vomiting without apparent cause. No abnormal findings were appreciated with the exception of mild gall bladder distension that was easily expressible. Medical management for suspected cholangitis was initiated and the patient was discharged. Three days post-operative, no further vomiting was noted, but increasing lethargy prompted an emergency visit to the primary veterinarian. An automated complete blood count revealed a neutrophilia with left shift and there was concern for peritoneal effusion. The patient was then referred to a referral Emergency Service. No free fluid was found on abdominal ultrasound and no significant abnormalities were identified with point of care bloodwork. Overnight supportive care resulted in significant clinical improvement and the patient was discharged. Eight days following discharge, the patient presented for hyporexia, lethargy, and vomiting within 5 minutes of eating. Abdominal ultrasound and two view abdominal radiographs were unremarkable. Supportive care was again initiated overnight. On the fourth day of hospitalization, a lateral thoracic radiograph was taken immediately following an episode of vomiting, and a presumptive type I sliding hiatal hernia was diagnosed. The patient underwent an abdominal exploratory surgery the following day with PEG tube placement to correct the hernia. Three days post-op the patient began vomiting immediately after tube feeding. Additional medical therapies did not improve the condition, and on recheck radiographs significant megaesophagus with presumptive esophageal stricture was appreciated. Endoscopy was completed the following day revealing two esophageal strictures. The first stricture was easily relieved with balloon dilation; however, the second stricture ruptured, prompting emergency surgery to repair defect. Three days following the procedure, repeat endoscopy showed a persistent caudal esophageal stricture with minimal luminal opening. Due to the poor prognosis, the patient was euthanized. This report will provide a brief discussion on hiatal hernias, with a major focus of esophageal strictures in companion animal species.