The year 2019 is an auspicious one, considering that the European Neighbourhood Policy (ENP) celebrates its 15th anniversary, whereas the Eastern Partnership, the multilateral dimension of the ENP towards the European Union (EU’s) Eastern Neighbourhood, is approaching its 10th anniversary. With this in mind, it is high time for EU decision-makers to ponder the region’s future prospects and to reflect on the key questions and answers regarding some of the most worrying concerns about Europe’s security and stability, concerns that also have global significance and impact.