The oil barge operation in Kaohsiung harbor is one of typical systems of resources allocation problems in a complex and dynamic environment. Such system is far more difficult to deal with than a static and deterministic system and often depends on experienced human experts for the oil barge assignment. One of the major dilemmas faced by the system is that decision makers do not know the managerial efficiency under the current dispatching mechanism. Besides, if the dispatching rules have been modified due to the resource variation in the future, how would the changes affect the system? The current research is trying to develop an evaluation system for oil barge assignment. The objective of the system is to evaluate the overall performances of the oil barge operation in Kaohsiung harbor. Both expert system and system simulation techniques would be applied for such analysis. To acquire the current heuristic of oil barge assignment and then transfer it to a rule-based knowledge in an expert system, the interview with the engineer, who is responsible for making such decision, is the crucial step. With the knowledge base and the reasoning mechanism available, it is possible to imitate the current oil barge assignment. To further evaluate the performance of such assignment rule, the current research has developed the system simulation model of oil barge operation. This model is able to quantify the service quality under various assignment scenarios. The results of simulation can further be presented to the decision makers with easy-understanding animations. The case study would focus on Kaohsiung harbor¡¦s oil barge operation. The integrity and suitability of the expert system and simulation model have been validated through extensive statistical analysis. At last, various scenario analysis based on such integrated models have been conducted to improve the current oil barge operation and to set the appropriate response plans confronted by the future development of Kaohsiung harbor as the Asia-Pacific transshipment center.