<p>Cognitive scaffolding is typically conceptualized in terms of environmental design which serves to offload, facilitate, or enhance the cognitive capacities of interacting agents. Recent contributions to the literature on scaffolding have noted that environmental design might likewise scaffold cognition in ways that undermine the interests of interactant agents—giving rise to notions of problematic or hostile scaffolding. Given the pervasiveness of social and technological scaffolding in contemporary life, the importance of understanding and assessing its effects can hardly be overstated. At the same time, however, the very pervasiveness of scaffolding raises a challenge to the current criteria for evaluating its effects by comparison with agents’ interests. This is because human agents and their interests alike are themselves the results of various forms of social and technological scaffolding. This paper explores the relationship between scaffolding and the formation of agents along with their interests, as well as the implications of this relationship for evaluating scaffolding as being hostile, neutral, or beneficial. I will argue that the formative aspect of scaffolding imparts a degree of uncertainty to evaluations of scaffolding based on agents’ interests. I will then demonstrate the relevance of the formative aspect of scaffolding in evaluating and assessing the potentially pernicious effects of contemporary social and technological scaffolding focusing on the examples of servitization marketing models and social and vocational digital infrastructures.</p>