Non-invasive ventilation is one of the major advances in respiratory medicine over the last century. It can be lifesaving for patients in acute hypercapnic respiratory failure, improving gas exchange and pulmonary mechanics and reducing the need for endotracheal intubation. Adherence to therapy is key to its success, and many patients find this a significant challenge. This case report will examine the pitfalls of initiating non-invasive ventilation, provide a brief overview of the current British Thoracic Society non-invasive ventilation guidelines, and describe common causes of a chronic obstructive pulmonary disease patient ‘failing’ non-invasive ventilation and an approach to the long-term management of the frequently exacerbating chronic obstructive pulmonary disease patient.