Ports can be considered as nodes in a (global) network and the accessibility of ports is an important indicator of economic performance. In addition, ports are important in modern societies and make a substantial contribution to the GDP of a city, a region or a country. To connect with the hinterland, ports make use of different modalities, such as trucks, trains, ships, and pipelines. But, at the same time, these modalities generate negative effects, such as emissions and noise, which need to be addressed. We call this the need for a more sustainable ports and hinterland connection. In this article we present a conceptual framework and simulation of sustainability measures and their effectiveness. The starting point of this framework is the identification of four different options, which can be considered as part of a dynamic (transport) system. These options can contribute to a (more) sustainable transport system, but the dynamics are the determining factor to assess its success. This paper combines the outcomes of both a qualitative and a quantitative study, and is structured in three parts. In the first part, on the basis of a literature study we discuss the dynamic relationships in the triangle: GDP, port-related transport, and sustainability. The second part, based on both a literature study and interviews, describes four options to improve sustainable port-hinterland transport performance. These options are presented in the context of a detailed analysis of feedback loops generated by the system dynamics (SD) model and a simulation study in the Port of Shanghai case. Finally, we consider the opportunities and limitations of these four options as an integrated part of the policy framework for the Port of Shanghai. One of the most important conclusions of this paper is that sustainable port related hinterland transport should be considered an organizational issue. The biggest challenge for the transition to a sustainable port related hinterland transport system is not to develop new technology (hardware or tech-ware), but to develop new governance arrangements (org-ware).