In this paper we discuss the application of simulation gaming to study the behavior and decision making of stakeholders when confronted with complex transportation problems. The problem we tackle is synchromodal transportation. Synchromodality requires the vertical and horizontal collaboration of stakeholders in all the levels of decision making. To facilitate this, we develop four games designed in a way that meets the needs of decision makers in each level. We present both board and digital games and the results from the first gaming sessions with Dutch supply chain and logistics professionals.