The chain of events and developments in Southeastern Europe during the 1990s provoked increasingly sophisticated political reactions, political approaches and long-term strategies towards the region on part of the European Union. The history of the Southeast European region has no better example of a “benign” external engagement than two dialectically interacting principles: regionality and conditionality. The need for adequate European Union strategies in meeting the challenges of the Southeast European region stems from two major factors: the existence of security risks and instabilities and the necessity of differentiated pre-accession of Southeastern Europe. The systemic nature of the main security risks and instabilities, stemming from the structural causes, legacies of the past, the ethnic and religious diversity of the area, its heterogeneous social contents and specific individual countries policies and political cultures, requires a complex system of interrelated and interacting European Union strategies with sophisticated management of their implementation. European Union strategic approaches to Southeastern Europe should reflect a vision of over-coming the structural causes of mid- and long-term instabilities and security risks.