Every year, more than 11 million maritime containers and 11 million commercial trucks arrive to the United States, carrying all types of imported goods. As it would be costly to inspect every container, only a fraction of them are inspected before being allowed to proceed into the United States. This dissertation proposes a decision support system that aims to allocate the scarce inspection resources at a land POE (L-POE), to minimize the different costs associated with the inspection process, including those associated with delaying the entry of legitimate imports. Given the ubiquity of sensors in all aspects of the supply chain, it is necessary to have automated decision systems that incorporate the information provided by these sensors and other possible channels into the inspection planning process. The inspection planning system proposed in this dissertation decomposes the inspection effort allocation process into two phases: Primary and detailed inspection planning. The former helps decide what to inspect, and the latter how to conduct the inspections. A multi-objective optimization (MOO) model is developed for primary inspection planning. This model tries to balance the costs of conducting inspections, direct and expected, and the waiting time of the trucks. The resulting model is exploited in two different ways: One is to construct a complete or a partial efficient frontier for the MOO model with diversity of Pareto-optimal solutions maximized; the other is to evaluate a given inspection plan and provide possible suggestions for improvement. The methodologies are described in detail and case studies provided. The case studies show that this MOO based primary planning model can effectively pick out the non-conforming trucks to inspect, while balancing the costs and waiting time.