This article proposes a rethinking of approaches to compliance, extending perspectives that view regulation as an interactive or reflexive process mediated by sociolinguistic 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. The article explores the question of interpretation of rules and the problem of avoidance and game playing. It reexamines 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. 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. It argues 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 article concludes by considering some of the current proposals for improving tax compliance, in particular by reducing complexity, improving clarity, and the use of broad principles.