The brief focuses on a key priority in European Union policy towards the east and south: the effort to turn the external border areas into secure, stable and prospering regions via support for cross-border cooperation on the local and regional level. This features highly in a range of policies brought together under the European Neighborhood Policy and in the partnership with Russia. The brief establishes that the mode of cross-border cooperation outlined in such policy initiatives frequently does not live up to expectations in the targeted regions and investigates potential reasons for this. The brief thus covers on-the-ground problems and practices with implementation of particular EU policy instruments that accompany ENPI: requirements of stakeholders’ partnership, for example. Political-administrative and civil society interactions, as well as their intersection, hence constitute main themes throughout the paper.