Across societies, cultures, and political ideologies, autonomy is a deeply valued attribute for both flourishing individuals and communities. However, it is also the object of different visions, including among those considering autonomy a highly valued individual ability, and those emphasizing its relational nature but its sometimes-questionable value. A pragmatist orientation suggests that the concept of autonomy should be further specified (i.e., instrumentalized) beyond theory in terms of its real-world implications and usability for moral agents. Accordingly, this latter orientation leads us to present autonomy as an ability; and then to unpack it as a broader than usual composite ability constituted of the componentabilities of voluntariness, self-control, information, deliberation, authenticity, and enactment. Given that particular abilities of an agent can only be exercised in a given set of circumstances (i.e., within a situation), including relationships as well as other important contextual characteristics, the exercise of one’s autonomy is inherently contextual and should be understood as being transactional in nature. This programmatic paper presents a situated account of autonomy inspired by Dewey’s pragmatism and instrumentalism against the backdrop of more individual and relational accounts of autonomy. Using examples from health ethics, the paper then demonstrates how this thinking supports a strategy of synergetic enrichment of the concept of autonomy by which experiential and empirical knowledge about autonomy and the exercise of autonomy enriches our understanding of some of its component-abilities and thus promises to make agents more autonomous.