This article reflects on the implications of the concept of health and the questions it poses for moral philosophy, psychology, and the panoply of professions that are involved in the practices of care and in the ethics of individual rights, dignity, and autonomy. Significant among these questions is what we call “the predicament of agency.” The predicament involves the ethical tensions—arising within the broad concept of health and flourishing, but also in concrete everyday practices and relationships—between supporting individual health outcomes and supporting health and flourishing through respect for autonomy and self-direction. Three ways of addressing the predicament of agency are discussed: by reinterpreting the nature and requirements of autonomy (a) by appeal to reason, (b) by designing or curating contextual conditions influencing choice (often called “choice architecture” or “nudging”) in ways that constrain autonomy but do not violate its core value, and (c) by appeal to relational judgment and reflective professional practice. The article argues that each of these lines of thought is important, but none is a panacea, and none is free from conceptual confusions and ethical pitfalls of its own. The relational approach is the most promising in pointing beyond the predicament of agency—not so much by resolving it as by showing how it can be worked through without either turning our back on caring or turning caring into management and manipulation.