Enterprise software system (ESS) design is premised upon an embedded business process model–a system model, which embodies the ESS designers' a priori view of best business practices in the intended context. In contrast, an organization's existing business model reflects its own a priori view of best practices. This native model is the aggregate of the organization's business processes, and operationalizes management intentions. Understanding process disparity between these models may improve the understanding of misalignment between ESS and the organization. Researches and practitioners struggle to explain how to achieve alignment and realize business performance from strategic IT investments. In this study, we consider the impact of misalignment between potential IT affordances and organizational capabilities on organizational strategies. We rely on interpretive case methodology to inform our investigation.