This article explores the European Union’s (EU) democratic and security objectives in the European Neighborhood Policy (ENP) toward three post-Soviet states: Georgia, Moldova, and Ukraine. By discussing the ENP’s objectives, this study concludes the following: first, despite long-term ENP democracy promotion, there have been very limited democratic developments in the partner states between 2005 and 2014; second, security challenges remain in partner states in the breakaway regions in Transnistria in Moldova, Abkhazia and South Ossetia in Georgia, and Crimea, Donetsk, and Luhansk in Ukraine. Therefore, EU’s Kantian view of security through democracy has failed, and its ambition to create a ring of Eastern friends has not led to improved relations in the Eastern neighborhood. On the contrary, the EU’s push eastward has instead intensified insecurity in its partner states due to limited democratization.