Due to technological, economic and spatial developments, various inner-city industrial areas with cultural-historical valuable elements, have lost their former use and their original economic value. Governments, private parties, citizens and interest groups in urban redevelopments are often convinced of the desirability of preserving this cultural heritage. However, transformation processes are complex and especially financial agreements seem hard to attain when plans have to be made effective. Recent planning approaches argue that urban developments are shaped through the interaction of many different stakeholders. As interests conflict, negotiation is needed to reach decisions regarding long term vision, short term actions and organizational and financial settlements. At some moments in the process the actors will cooperate, while at other moments they will compete. This paper gives insight in the interaction processes and the encountered difficulties in urban redevelopments with cultural heritage. In particular, an attempt is made to identify barriers and drivers of complex collaborative planning projects. Therefore, we conducted an explorative case study of ten urban redevelopment projects with cultural heritage in the Netherlands. Based on an analytical framework, we identified important differences and similarities between the cases, and analyzed whether and how project and interaction characteristics have implications for project performance. The results can be used for further research or for process improvements