This article first introduces both the technical and business environments in which Web information systems are developed and the unique project variables of these systems. Characteristics are identified where e-business projects differ from traditional information systems projects. The next section presents various system development methodologies, provides a categorization framework and analyzes these categories for situations where each is best utilized. The synthesis of applying the environmental and project variables to the system development methodology categories provides the main contribution of the article. Conclusions are drawn that a project is unlikely to align perfectly with any one methodology. The project manager should select the methodology that is the “best fit” from the model presented here. Finally, the project manager should customize the process based on the unique characteristics of the organization, project, and team.