A 69-year-old Caucasian man, who had been discharged 2 days previously, 5 days post-elective right total hip replacement, was re-admitted with a 16 h history of coffee-ground vomiting and epigastric pain. He had been discharged with 220 mg dabigatran, a novel oral anticoagulant. The coffee-ground vomiting started within minutes of taking the first dose. Haemodynamic compromise, agitation, decreasing conscious level and aspiration pneumonia necessitated intubation, ventilation and inotropic support in the intensive care unit. A CT on admission showed extensive intramural air seen within the lower oesophagus and a dilated stomach, duodenum and jejunum. Endoscopy of the upper gastrointestinal tract showed extensive ulceration, sloughing and multiple areas of necrosis in the distal oesophagus and stomach. The patient made a fully recovery with supportive management.