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Past literatures on e-learning system and courseware have focused on the system features and on the technologies employed. To integrate IT well with pedagogical principles, it is important to involve instructors in the courseware development. This study seeks to gain insight on courseware development by investigating instructor's different roles in each courseware development phase. Using an educational system development model and role theory as theoretical lens, this research conducts multiple case studies involving three sets of language courseware and reveals that courseware development is a gradual process requiring dynamic role playing of the instructor. Lessons are drawn from the case study to improve courseware development efficiency by facilitating instructors' role transition and reducing their role overload and role ambiguity. Theoretical and practical implications of the process-based role framework are discussed.