This paper was written in the context of the DIAMOND SBO project. Against the background of a growing concern over increasing market power by a handful of widely used online services, this paper starts from the assumption that such a situation may limit citizens’ access to or consumption of a diverse set of media content. Consequently, this would have a negative impact on citizens’ fundamental right of access to information, which would affect media pluralism in general. This assumption sparks the question if the rise of such new digital media services necessitates a reconceptualization of existing monitoring frameworks for media pluralism. The development of practical indicators that are capable of measuring media pluralism in the online environment would allow more accurate monitoring of the situation. This could introduce more transparency of the online media environment, in turn enabling public scrutiny. Considering the complex nature of this environment however, close cooperation and interaction with various stakeholders based on a minimal consensus and understanding of the issues at hand are essential while developing relevant indicators. Therefore, this paper integrates the results of empirical studies with various stakeholders with the evaluation of the legal and policy framework for monitoring media pluralism in and for the Flemish community in Belgium specifically.