An elderly lady, known with a background history of Alzheimer’s dementia, gastro-oesophageal reflux disease and a reported history of self-induced vomiting, presented to our emergency department with a two-day history of vomiting, diarrhoea, anorexia, and malaise. Initial clinical examination and investigations only demonstrated mild dehydration. Despite a satisfactory response to initial symptomatic treatment, with complete cessation of vomiting, the patient had a recent sudden deterioration. Due to continued forcible belching, it was found that she had developed a sudden onset of back pain and subcutaneous emphysema. A CT scan showed mid-oesophageal rupture along with pneumomediastinum and bilateral pneumothoraxes. The patient was subsequently diagnosed with Boerhaave syndrome. Due to her clinical factors and the risk of surgical management, it was decided that she should be managed non-operatively with oesophageal stenting and bilateral chest drains, which was met with a good clinical course and outcome.