In this paper, we demonstrate the complexity of intermediation in practice. Intermediaries are seen as crucial actors in a transition process, but so far the transition intermediary literature has had a positive bias towards their role. We mobilize strong structuration theory to develop an analytical perspective that captures how complexity, tensions, and ambiguity influence the transition intermediary’s role and activities. We apply the perspective to the case of Connecting Mobility, a transition intermediary in the Dutch smart mobility field. Results show that Connecting Mobility has fulfilled several transition intermediary roles to different degrees, both simultaneously and sequentially, but they also experienced difficulties in fulfilling these. We conclude that the roles and the engagement of transition intermediaries in meaningful activities are a response to their dynamic context and internal learning processes. As an additional consequence, a single transition intermediary’s direct impact on the overall transition process should not be overstated.