The goal of this chapter is to provide a conceptual analysis of ethical hacking, comprising history, common usage and the attempt to provide a systematic classification that is both compatible with common usage and normatively adequate. Subsequently, the article identifies a tension between common usage and a normatively adequate nomenclature. ‘Ethical hackers’ are often identified with hackers that abide to a code of ethics privileging business-friendly values. However, there is no guarantee that respecting such values is always compatible with the all-things-considered morally best act. It is recognised, however, that in terms of assessment, it may be quite difficult to determine who is an ethical hacker in the ‘all things considered’ sense, while society may agree more easily on the determination of who is one in the ‘business-friendly’ limited sense. The article concludes by suggesting a pragmatic best-practice approach for characterising ethical hacking, which reaches beyond business-friendly values and helps in the taking of decisions that are respectful of the hackers’ individual ethics in morally debatable, grey zones.