Increasing global competition and advances in Internet technologies have led organizations to consider e-business strategies. However, evolving e-business strategies have been identified as a critical issue faced by corporate planners. The relevance and the use of IS (Information Systems) strategy planning practices in the context of e-business have been argued among researchers. In this paper, the authors investigate whether organizations can successfully improve the IS value in the e-business context by suitably extending and modifying IS planning practices. To achieve this objective, the authors use a longitudinal case study of an Indian automotive manufacturer to critically evaluate â€˜whyâ€™ and â€˜howâ€™ e-business strategies differ from IS strategies. The authors compare and analyze five important planning parameters (strategic alignment, technological environment, formalization, role of the IS function, and implementation planning) and the IS value of both IS and e-business contexts. The research reveals that the e-business contexts are characterized by significant changes in planning parameters. Extending IS planning experiences and proper management of these parameters results in successful e-business strategies. The paper is concluded with a set of implications for deploying e-business strategies in developing countries and directions for future research.