Nasogastric tube (NGT) insertion is a common procedure performed by residents and nursing staff to access the stomach. Although an apparently simple procedure, it is associated with technical difficulties and complications if proper care is not taken during insertion. We present a case of a 79-year-old female with multiple comorbidities who had a percutaneous enteral gastrostomy tube removed due to infection of an insertion site wound and a NGT was inserted for feeding. A few minutes post-insertion the patient developed shortness of breath and a drop in oxygen saturation. An immediate chest X-ray showed the NG tube traversing along the course of the trachea and the right main bronchus into the right upper abdomen with right-sided pneumothorax. The NG tube was immediately removed and a right chest drain inserted. Subsequent imaging showed right-sided pneumothorax with evidence of lung laceration and underlying lung collapse and diaphragmatic injury. The patient underwent a prolonged course of hospitalisation due to hospital-acquired pneumonia before being discharged upon clinical improvement. We highlight the fact that a simple and routine procedure such as NGT insertion can have devastating complications if due care is not taken. Along with a literature review, we provide and compare different methods to confirm correct placement of a NGT. The article also discusses important pearls for practising physicians and nursing staff to avoid such complications. Owing to the frequency of the procedure in hospitals and long-term care units, appropriate awareness among medical staff is necessary.