Ukraine’s participation in the European Neighbourhood Policy (ENP) is characterised by several paradoxes. First, the ENP was conceived (Batt et al. 2003) as a framework for engagement for Ukraine as an alternative to enlargement. This accounts for its frosty reception in Ukraine. The second paradox is that, while critical of the policy, Ukraine successfully used the ENP to upgrade its bilateral relations with the European Union (EU) to that of an Association Agreement (AA). The third paradox is that while Ukraine was a demandeur in relations with the EU, the Ukrainian authorities have been slow in implementing domestic reforms – an essential pre-condition for integration with the EU. The ENP did not provide incentives that could sway the incumbent elites in favour of domestic reforms, or even into signing the coveted AA, when presented with a counter-offer and incentives from Russia. The failure by President Yanukovych to sign the AA in 2013 triggered a powerful domestic backlash, ending his regime in early 2014, and generated a response from Russia, which culminated in the annexation of Crimea and support for separatism in eastern Ukraine. It was Russia’s actions, and the election of new political forces in Ukraine in 2014, that gave the strongest impetus to reforms since the country obtained independence in 1991. Central to these reforms is a drive for integration with the EU, premised on the broad consensus in Ukraine that the country ‘has nowhere else to go’. The fourth paradox is that Russia’s punitive actions against Ukraine’s European choice vastly increased Ukraine’s dependency on the EU, imbuing the latter with disproportionate influence – something that the ENP on its own failed to achieve. This chapter analyses Ukraine’s participation in the ENP to illuminate these four paradoxes.