One of the contemporary challenges involves a type of dispute in the digital environment where the law does not contain a rule that was created intentionally for such cases but a legal rule can be found that was created for similar cases in the non-digital environment (e.g., copyright infringement online compared with making copies of a cassette tape). This chapter explores how courts reason in the face of such a dilemma. Two patterns in judicial decisions can be found – consideration of (a) the purpose and function of the disputed objects or actions, and (b) the extent of harm or damages caused by the behaviour in question. The former has the potential to be worded as a principle that ‘similar actions or objects in different contexts receive a similar legal treatment if their purpose and function does not differ’, and the latter, as a principle that ‘an act which is incompatible with the text of the law but causes no harm or any risk of it will be treated as lawful’ and conversely, ‘an act which causes harm or the risk of it will be treated as unlawful, even if its incompatibility with the text of the law is vague’.