This article formulates a conceptual and analytical contribution to investigations of agency in transitions. Transition studies often assume, rather than assess, structure-agency dynamics through conceptions of a ‘nested hierarchy’ between, or a ‘structuration continuum’ within, niches and regimes. Neo-institutionalist and practice theoretical approaches have provided tools for more precise investigations of this interplay, like institutional logics, institutional work, and the de-and re-routinization of habits. Yet, both also struggle to adequately reveal how structures enable or constrain action and how actors build structures. We introduce transactional pragmatism, with its focus on how actors and their context are in constant functional coordination, to further develop the concept of habits as a central mechanism through which the process of de- and re-routinization takes shape in action. We draw on Practical Epistemology Analysis and the concept of privileging to suggest analytical concepts and questions for facilitating future research on the topic.