This article analyses what may be termed as the European Union’s (EU) post-liberal approach to the Moldova–Transnistria conflict. Since 2003, within the ENP framework, the EU has become increasingly committed to its transformation. Such an engagement is further confirmed by the establishment of the European Union Border Assistance Mission to Moldova and Ukraine (EUBAM) in 2005, aimed at building confidence between the parties, stimulate their economic interdependence and change perceptions about the conflict. The mission’s outcomes are moving beyond its technical scope, supporting the conflict peaceful transformation. The focus on bottom-up initiatives and local engagement allows for a broader understanding of the complex dynamics underlying the conflict, which together with the high-level negotiation process may provide a holistic approach to its resolution and increase the likelihood to reach a sustainable settlement.