Non-steroidal anti-inflammatory (NSAIDs) drugs are a group of medications acting through cyclooxygenase (COX-1) and cyclooxygenase (COX-2) enzymes inhibition. Hypersensitivity reactions to NSAIDs, although not rare, are poorly characterised and often go undiagnosed especially in children. We present in this paper a case of ibuprofen anaphylaxis that exemplifies the challenges involved in diagnosis and management of hypersensitivity reactions to NSAIDs.