This article examines the role of punitive remedies in English and Italian contract law. Firstly, it attempts to define punitive remedies and compares them to similar, but distinct, awards. Then, the article asks whether punishment is an inherent element of contract, and analyses the answers given by different Anglo-American contract theorists; in doing so, it differentiates between the voluntaristic and non-voluntaristic schools of thought, but also notes a substantial divergence in views within each school of thought. Turning to the positive law, the article assesses whether punitive damages are a part of English contract law and, if not, whether they are likely to be recognised in the foreseeable future. Lastly, the article engages in an analogous assessment of Italian contract law, identifying similarities and differences between the two jurisdictions. It concludes that, although there are significant differences in the remedial regime employed in England and Italy, both are governed by an underlying reluctance to use contract law as a tool for deterrence and retribution.