Following the necessity for spatial planning to focus on ‘what works’ in terms of implementation and policy delivery, during the last decade, the notion ‘soft’ spaces of cooperation have been in the spotlight of many academics working on territorial cooperation units. ‘Soft’ spaces of cooperation have been introduced mainly to explain what was happening for real through the continuous attempts to promote new policy scales, initially through the device of fuzzy boundaries. However, despite the necessity to address interests beyond existing rigid administrative boundaries, still issues related to financial power, infrastructure coordination and investment, ecological and environmental concerns, etc., all are situated within hierarchical structures of government and governance. Challenges arise and affect the interaction of actors in these areas, given the different institutional and cultural settings. This research investigates ways in which governmental institutions influence the coordination between non-governmental actors, points of interests that can foster the cooperation between governmental institutions and, more specifically the main challenges that non-governmental actors face while trying to cooperate due to cultural differences and institutional set-up in a ‘soft’ territorial cooperation. The research has been carried out in the Dutch-German border area, focusing on a common natural linkage and asset such as the Rhine river. While coordination between different sectoral policies exists in both sides of the border, different social context, planning mode and different legal and political conditions make the implementation of common projects a challenge.