Nasogastric tube insertion is a commonly performed procedure that can be associated with significant morbidity and even mortality. There is no universally accepted technique to confirm correct placement. Most confirmatory methods are performed after placement, therefore misplacement and potential complications may have already occurred. We report a case where a commonly used bedside confirmatory test gave false reassurance that the nasogastric tube was properly positioned, but a plain chest X-ray revealed a massive pneumothorax due to inadvertent intrapleural placement of the tube. Due to the deficiencies of traditional confirmatory bedside techniques, and the limitations of modern and more sophisticated confirmatory methods, the plain chest X-ray remains the gold standard test to confirm correct nasogastric tube placement. We appraise the methods commonly employed to confirm nasogastric tube placement, and discuss factors that may increase the risk of misplacement.