The aim of this article is to identify the contexts and conditions that allow for successful education transitions and opportunities for the Roma minority in Europe. Thus far, transnational and national policies have failed to ensure Roma inclusion and education equality, even though some progress is visible. Using a combination of policy analysis and interviews with NGO and European Union actors, University academics and Roma students, the article examines the key contexts that frame education policies and create the necessary conditions for education transitions. It identifies the problems and challenges within the contemporary EU education policy frameworks and highlights the tensions between political rhetoric and policy commitments that are visible at national, transnational, and local levels. In addition, through a focus on individual student experiences, the article captures the lived reality of Roma students who have managed their education transitions with success.