Financial institutions are striving to maximize benefits from the emerging digital economy. However, the decision to take such an investment option is contingent upon the "preparedness" of these institutions and the attributes of the infrastructure of global transactions. While the migration to global spaces of operation is being relaxed by the proliferation of information technology infrastructures, the deployment of web based decision support systems is still constrained by many data-specific and decision modeling limitations. To move these systems to a stage of engagement, a paradigm shift in terms problem conceptualization, system analysis and design is looming big. This paper reflects on these limitations with special emphasis on the investment information systems. Key words: Web based DSS, investment DSS, decision making.