This paper describes the approach for courseware simulation learning tool development that able to assist the students on learning and understanding their courses specifically on supply chain. A courseware simulation prototype called Operation and Supply Mini Simulator (OSMS) is being developed for deployment in interactive learning. A courseware development lifecycle is proposed with combination of empirical approach and prototyping model to allow iterative user’s requirement gathering and to build optimal control application. The proposed OSMS offers an innovative learning tool that mimics the graphing calculator. The features in the tool enable students to compute and visualize graph data for multi-mode analysis in order to develop higher understanding on the supply chain course.