Metastructuration actions (overarching activities from (top)- management that shape and align users’ activities of IS/IT use) are often advocated to improve the success of IS/IT implementation. But is the potential of these actions situational to the interactions between different stakeholders; and if so, how can this context be taken into account? This key question is addressed in this paper. Building upon Orlikowski et al., the situational effect of metastructuration interplay concerning four key stakeholders; (top) management, users, IT department, and external service providers or consultants is explored. The empirical case context is a Dutch public healthcare organization that deployed three departmental information systems. Based on 26 qualitative stakeholder interviews, it was found that three types of metastructuration actions were critical, which are particular related to two types of stakeholder context. It is concluded that the stakeholder context is indeed conditional to metastructuration actions, and also to the success of IS/IT implementation in terms of perceived system quality and acceptance of the systems.