This chapter explores the evolution and techniques of corporate tax arbitrage, focusing on how multinational corporations (MNCs) exploit the structural features of the international tax regime. It traces the origins of the system to the 1928 League of Nations framework, which privileged source and residence taxation while neglecting valuation and the treatment of intangible assets. This omission, combined with the legal autonomy granted to subsidiaries within centrally coordinated multi-corporate enterprises, created enduring arbitrage opportunities. The chapter analyses how firms leverage intangible assets, ownership structures, and corporate residency rules to reallocate profits across jurisdictions, exploiting regulatory mismatches. It highlights the role of offshore financial centres (OFCs), intermediary subsidiaries, and hybrid instruments in enabling tax avoidance. Case studies – such as Apple’s use of stateless entities and Amazon’s transfer of losses via Luxembourg – illustrate how MNCs circumvent tax rules through entity design, subsidiary chaining, and strategic use of global value chains. Using new evidence from the CORPLINK study, the chapter estimates that although OFC intermediaries represent only 1.7 per cent of subsidiaries among the world’s top 100 non-financial firms, they control up to two-thirds of group revenues. Tax arbitrage is shown to be systemic, not exceptional, and embedded in contemporary corporate structures.