A 65-year-old male with a long history of congestive heart failure presented to the emergency room with facial swelling 7 h after the first dose of enalapril. He was treated with diphenhydramine and hydrocortisone which improved his angioedema. However, there was a profound relapse of the angioedema followed by respiratory arrest. He suffered severe anoxic brain damage and died five days later. It is likely that the long half-life of enalapril lead to this rebound phenomenon. Enalapril induced angioedema is reviewed with suggestions for management.