Punishment can be seen as a moral exchange through which the messages that are (explicitly or implicitly) communicated via punishment are critical in facilitating offenders’ acceptance of their punishment, legitimacy of authority and social norms, and ultimately, behavioural reform and deterrence of future crime. This research examines (a) the types of messages transgressors receive through punishment (why they think they are being punished), and (b) transgressors’ reactions to them (e.g. perceived fairness, experienced remorse). Further, it explores (c) the features of a punitive message that influences how the message is interpreted by transgressors. In particular, the project examines whether the “quality” of the interaction between decision-makers (i.e. punishers) and transgressors—as experienced through social dynamics of the court process, such as expressing empathy and respect to transgressors, and giving them voice—influences the way transgressors approach and make sense of their punishment. The insights from this research has important implications for how we should deliver punishment to enhance justice outcomes, whether in the context of formal legal proceedings or informal sanctions.