Abstract The purpose of this study is to develope a specialized system software tool for Chinese Computer Assisted Instruction Courseware (CCAI) by way of using the concept and technique of file management system. Thus, it will reduce the time-consuming effort in programming and transforming the instructional material into CAI courseware. The main five points of this paper are in the following: A. Briefly describing the bottleneck of the Chinese CAI courseware implementation. B. Providing suggestional procedures for implementing a courseware. C. Describing the function and the system of the developed software CCAI File Management System. D. Showing the methods and processes in the transforming instructional material into CCAI courseware. E. Analyzing the mathematical file structure about this system.