A 64-year-old man without any significant medical history presented to accident and emergency department with haematemesis and melaena, quite similar to an upper gastrointestinal bleed. However, the unexplained left-sided neck pain with a history of overnight vomiting prompted further imaging. Air was visible in the soft tissues on a lateral X-ray of the neck, which led to a CT scan and this showed a proximal-mid oesophageal rupture. The patient was stabilised and transferred to a cardiothoracic unit for observation. An inpatient endoscopy did not detect a perforation and the patient was discharged 5 days later without any further complications. This case report highlights how a high oesophageal rupture can mimic an upper gastrointestinal bleed and also the need for further imaging when there is an incongruent history, so that appropriate care is provided to minimise mortality.