This paper problematizes the overall positivity of stakeholder engagement literature and analyses its grey area. We discuss the bright and the dark side of stakeholder engagement and identify the grey area in between these two sides. Based on a qualitative content analysis of 26 interviews collected from circular economy stakeholders in Finland, we identify three sources of the grey area of stakeholder engagement: the individual stakeholder, stakeholder relationships and the institutional context. According to our analysis, the grey area consists of challenges caused by individual resistance and individual inability, collaboration challenges, complexity caused by the diversity of perspectives, unpredictability caused by the political and legislative context and insecurity caused by environmental unpredictability. We argue that particularly in the context of a multi-stakeholder network, the grey area is a natural and unavoidable part of stakeholder engagement and thus, should also be explicitly recognized and discussed in the literature.