Taxation is key to the character and functioning of the state, economy and society. Its effectiveness and the levels of compliance greatly depend on acceptance by citizens of its legitimacy. This paper proposes a rethinking of approaches to compliance, extending perspectives which view regulation as an interactive or reflexive process mediated by socio-linguistic practices. These suggest that the meaning of rules is not fixed ex ante, but may emerge and change through such interactions, which therefore actually help to construct what it means to comply. The analysis supports proposals to base tax law on purposive general principles combined with detailed rules. However, it suggests that this should be the approach adopted for the tax code as a whole, instead of focusing mainly on the merits of a general anti-avoidance principle, as some of the recent debates have done. Although a general anti-avoidance principle may have a place, the aim of achieving a cultural shift in the regulatory system of tax compliance needs public debates on the substantive general principles of taxation. These have been neglected, as tax reform initiatives have tended to become fruitless exercises in trying to rewrite complex tax law in plain language. Unless the tax code itself is built on a sound foundation of principles generally accepted as fair, compliance will be problematic. The first part of this paper explores the question of interpretation of rules and the problem of avoidance and game-playing. It re-examines the issue of the indeterminacy of rules and relocates it within the context of professional and regulatory practices, suggesting that it is these interactions that construct the meaning of rules and hence of compliance. In the second part the analysis is applied to income taxation, to sketch out how the international tax system has been constructed through the interaction of contending views of fairness in the allocation of tax jurisdiction, while in the process becoming refined into a formalist and technicist process of game-playing. I argue that the central factor in this process has been the inherent contestability of the core concepts of international taxation, the rules on corporate residence and source of income. The final section then considers some of the current proposals for improving tax compliance, in particular by reducing complexity, improving clarity, and the use of broad principles.