Abstract: In the recent time, achieving sustainable development and excellence in higher education is anchored on effective development of courseware and its application in a web-enabled environment. The development of interactive e-learning courseware has focused largely on the instructional design approach of multimedia applications and has brought about a substantial amount of success in producing engaging multimedia educational resources. However, challenges associated with early stages of e-learning courseware development are significant when compared to those at the later stages. Addressing these challenges requires sensitivity to the process dynamics, besides the technical know-how. This study is based on an in-progress project to develop courseware material for online learning. The project was anchored by University of Ilorin, Committee on Courseware Development in conjunction with all the academic staff of the University. In this project, template was adopted as the developmental model to navigate the project through the early stages, with the intention of securing incremental progress. Within this developmental model, the paper then describes the intricacies of integrating instructional design principles and evaluation techniques to tackle the challenges of the evolving template. This study represents the reflections of the authors as practicing instructional designer and it should interest readers who want to see a stronger connection between the theory and practice of courseware development. The general reader may also find the concept of templating helpful, given the constant demand to innovate in the learning contexts and may well find some applicability for it in their own disciplines.