It is often thought that compliance with rules is inherently irrational, since it can never be rational to follow rules that lead to outcomes that are contrary to the agent's goals. If, however, rules provide the results desired by the agent, then compliance is inherently irrelevant, as the conduct prescribed by the rules cannot be said to make a difference in the agent's behaviour. In order to address these critiques (at least in part), scholars have developed non-deliberative approaches to rule-compliance based either on exclusionary reasons (Joseph Raz) or on stable plans (Scott Shapiro) that are implemented once factual conditions are satisfied, i.e.: if an agent made a stable plan to comply with legal rules, s/he would implement his/her plan once a rule is identified as being part of the legal system. Contrary to these rather sophisticated views, I stress the deliberative character of rule-compliance. I claim that rules might make a practical difference when they provide agents with epistemic inputs enabling the agent to change his/her beliefs about his/her preferences on options of behaviour. I further claim that if agents act based on their own assessment of the means of action, then new or experimental forms of governance aiming both at bridging the principal-agent gap and at the collaborative selection of means of action may be more suitable in ensuring compliance than traditional legal regulation. The second part of the dissertation revolves around the idea that the deliberative character of rule-compliance might affect cooperation in legal systems. Here, I examine Scott Shapiro's conceptualization of legal systems as joint intentional activities with authority, and claim that the authoritative-coercive character of the legal system might pose problems of irreconcilability with some of the features that are necessary for a joint intentional activity to exist. I subsequently examine the situation in which the common goal that officials in the legal system supposedly share is unable to guide their interpersonal behaviour. Finally, I discuss the possibility for interpersonal conflict to evolve into more cooperative scenarios.