Value creation from e-business for customers in healthcare is an important topic in academic and practitioner circles. This chapter reports the findings from a two-year research study, which found that disappointing results from the muchhyped application service provider (ASP) business model is currently being replaced by perceived new opportunities from Web services. Yet past failings from ASP do not guarantee future success with Web services models, particularly as evidence shows that accruing value-added benefits from e-business initiatives is often fraught with difficulty. Healthcare is no exception, and is likely to pose more problems given the complexity of the organizational structures, processes, procedures, and activities within this vertical sector. This research study calls for a more rigorous approach in identifying and evaluating key performance areas and indicators from new e-business initiatives involving emerging technologies and platforms such as Web services. Yet the measures and metrics used for healthcare may differ from those adopted in other sectors. Healthcare professionals will therefore need to develop context specific key performance areas (KPAs) and KPIs, and caution against accepting at “face value” the value proposition devised by Web service providers.