Beyond the national political-territorial borders in Europe, the cross-regional dimension maintains an experimental democratic character. Entities developed to foster cross-border cooperation, such as working communities and Euroregions, are conceived as mechanisms of democratisation through the decentralisation of regional or/and local governmental bodies. However, scholarly debate suggests that the top-down policy-making process that is characteristic of cross-border programmes seems to cast doubt on the fulfilment of a European participatory democracy. In this respect, the cross-border cooperation process seems to contribute an added value to the dilemma of the European democratic deficit. The objective of this paper is to present a regional contribution to this debate through a study of local experts’ perspectives on the implementation and impact of cross-border cooperation policies in the southern Portugal–Spain border region and the possibilities for local and social participation. This paper utilises data from two related investigations in the southern cross-border area between Portugal and Spain, including qualitative interviews, focus groups and content analysis of secondary data. The results reveal a positive attitude towards the recent regional top-down initiatives of European integration, although local experts question the potential for the inclusion of local perspectives in cross-border initiatives. In addition, during this period of economic crisis, political contradictions may be observed, and political initiatives related to the Spanish–Portuguese border may hamper the existing cross-border flows and dynamics of progressive integration. In this sense, local authorities play an important role as the nexus between transnational institutions of cross-border cooperation and the inhabitants of border regions.