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This chapter examines the causes of failure in a Web-based information system development project and finds out how complexity can lead a project towards failure. Learning from an Information System Development Project (ISDP) failure plays a key role in the long-term success of any organization desirous of continuous improvement via evaluation and monitoring of its information systems (IS) development efforts. This study reports on a seemingly simple (but only deceptively so) failed ISDP to inform the reader about the various complexities involved in ISDPs in general, and in developing countries in particular. An existing framework from contemporary research is adopted to map the complexities found in the project under study and the critical areas, which lead to the decreased reliability and failure in Web-based information system development, are highlighted.