The tragic events of 9/11 resulted in an accelerated, substantive increase in cross-border regulations, programs and the application of technologies like Intelligent Transportation Systems (ITS) to address security concerns. The entire length of the supply chain has been identified as a key area where security must be enhanced; indeed, security is currently the highest priority concern in cross-border and international transportation. At the same time, service quality for all users – as well as economic cost to both the transportation industry and public infrastructure providers – must be assessed in light of these expanded security requirements. Both the public and private sectors must make decisions on the implementation of new security initiatives and investment in enabling information technologies, human resources, infrastructure, and organization changes. The necessary Benefit-Cost and Return on Investment calculations depend very much on the accurate estimation of how process changes impact security, productivity, service and cost. Benefit and cost estimation can be improved through the use of process mapping and simulation models, which can efficiently estimate process change impacts under different regulatory and information technology scenarios. The process mapping approach is especially useful in measuring firm specific impacts on private sector stakeholders and the tradeoffs that may occur in the supply and transport chains moving products across borders. This paper describes the process mapping of cross-border trucking from Canada into the United States and demonstrates how simulation modeling based on the mapping of the cross-border transport chain can be used to identify and quantify strategic and operational choices in both the public and private sector. The process mapping research is part of a larger program mapping the supply chain of all modes involved in border transportation.