Although the interactions between information technology and the context of government-to-business relations challenge the implementation of information systems, the challenges are currently under-researched. Therefore, this paper analyzes the mutual shaping between technology integration and the context. Based on an empirical study of the deployment of electronic cash registers for value-added tax administration, the analysis explains how government-business dialectics inform the design of relations between institutional, technological and organizational factors. The explanations lead to the argument for a dialectical design perspective on implementation that facilitates a systematic comprehension of (1) the inducements of design; (2) the relationships between the factors as design qualities; (3) the real and perceptual characteristics that define the soundness of the system; and (4) the paradigmatic distinctions between institution-organization design, organization-technology redesign, and functionality design of technology. This perspective leads the conceptualization of implementation in this context, and overcomes the limitations associated with the notable existing perspectives.