While the paradigm for organizations evolves into an information perspective and information systems’ (IS) role shifts from efficiency to effectiveness, among the top issues of IS management is measuring and improving IS effectiveness. This chapter offers an IS effectiveness evaluation methodology applied on a government organization in Turkey. IS maturity is taken as a reference for determining independent variables of the research. The chapter supports that “IS effectiveness” is a relative term conceptualized by organizational features. The case study suggests future research areas. A number of findings and propositions have been presented, including the alignment of technology and business process, integrating stakeholders’ trust and commitment, the significance of top management support, top-down vs. bottom-up approaches, which can enhance the adoption and institutionalization of information systems implementations within a government organization.