The EU–Ukraine Association Agreement famously featured as one of the available models in the EU chief Brexit negotiator Michel Barnier's scale of options for the UK–EU post-Brexit future relationship, sandwiched between the EU– Swiss system of bilateral agreements and the EU–Turkey Customs Union. It was selected by the European Commission in view of its comprehensive scope, covering political dialogue and coordination of foreign policy, justice and home affairs, trade, economic and social matters, as well as a considerable depth of legal commitments which, if sufficiently implemented, would offer significant opportunities to access the EU internal market. As was stated by the then European Council president, Herman Van Rompuy, at the time of its inception the EU–Ukraine Association represented the most advanced framework of relationships ever concluded between the EU and a third country.

Yet the Agreement's origins and its evolution were taking place in a markedly different political context compared with the EU enlargement history from 1973 onwards. First, from the political perspective, the EU was placing its relationship with Ukraine and other countries of the former Soviet Union on a different conceptual premise as compared with the EU pre-2004 neighbours in Central Europe, avoiding a political commitment towards their EU membership perspective, as well as taking a cautious approach towards closer trade ties and economic cooperation in the first generation of bilateral agreements, known as Partnership and Cooperation Agreements (PCAs). Only after the 2004 EU enlargement, as the success of transformations in the candidate countries was attributed to the transformative power of the pre-accession processes, did the EU start to contemplate ways of replicating the winning formula without the apparently high political, institutional and economic costs of continued expansion. The European Neighbourhood Policy (ENP) sought to substitute the membership perspective instrument by a carefully calibrated idea of a “stake in the EU Internal Market” achievable through consistent, enforceable and verifiable processes of legislative approximation to the EU's acquis communautaire and accompanying institutional reforms in the partner countries.