The significance of seaports in enabling global trade and impacting global supply chains require them to operate efficiently. Due to the required interactions, seaports are not only affected by their operations, but by other parties in the transport chain. The existing interactions between multiple parties in the transport chain add complexity to the system. Using Jordan as a case study, and focusing on containerized transport, this paper develops a System Dynamics framework that assesses the impact of alternative strategies on the container transport chain. The paper first identifies the sub-systems in the Jordanian container transport chain, to introduce a conceptual model that illustrates the causal relations in the system. A System Dynamics framework is then presented to assess the impact of different strategies on the container transport chain. Based on industry trends in reducing container delivery time and adding capacity at the terminal, three different alternatives are introduced and simulated under multiple scenarios. The list of alternative strategies includes: investing in the hinterlands, implementing technology to reduce documentation processing time and a combination of both. The simulation output shows while the first alternative reduces the dwell time by over six days, it does not reduce delivery time. The second alternative is extremely effective in reducing delivery time but does not add resilience to the terminal’s capacity. The third alternative is the highest ranking in terms of delivery time and container turnaround. Simulating the third alternative again over a longer period shows that it outperforms the current alternative for up to 275 days only. The third alternative resulted in an increase in fleet utilization, which ultimately leads to a congestion in the terminal. Thus, a holistic view needs to be taken when assessing the impact of different strategies and ensuring the right KPIs are chosen. The presented framework is highly relevant to decision makers including policy makers and investors in Jordan and elsewhere. For Jordan, with government plans to reduce container dwell time, the framework provides added insights for decision makers, beyond the seaport.