The efficiency of current cargo screening processes at sea and air ports is largely unknown as few benchmarks exists against which they could be measured. Some manufacturers provide benchmarks for individual sensors but we found no benchmarks that take a holistic view of the overall screening procedures and no benchmarks that take operator variability into account. Just adding up resources and manpower used is not an effective way for assessing systems where human decision-making and operator compliance to rules play a vital role. Our aim is to develop a decision support tool (cargo-screening system simulator) that will map the right technology and manpower to the right commodity-threat combination in order to maximise detection rates. In this paper we present our ideas for developing such a system and highlight the research challenges we have identified. Then we introduce our first case study and report on the progress we have made so far.