In everyday situations, and particularly in some sport and working contexts, humans face an inherently unpredictable and uncertain environment. All sorts of unpredictable and unexpected things happen but typically people are able to skillfully adapt. In this paper, we address two key questions in cognitive science. First, how is an agent able to bring its previously learned skill to bear on a novel situation? Second, how can an agent be both sensitive to the particularity of a given situation, while remaining flexibly poised for many other possibilities for action? We will argue that both the sensitivity to novel situations and the sensitivity to a multiplicity of action possibilities are enabled by the property of skilled agency that we will call metastable attunement. We characterize a skilled agent’s flexible interactions with a dynamically changing environment in terms of metastable dynamics in agent-environment systems. What we find in metastability is the realization of two competing tendencies: the tendency of the agent to express their intrinsic dynamics and the tendency to search for new possibilities. Metastably attuned agents are ready to engage with a multiplicity of affordances, allowing for a balance between stability and flexibility. On the one hand, agents are able to exploit affordances they are attuned to, while at the same time being ready to flexibly explore for other affordances. Metastable attunement allows agents to smoothly transition between these possible configurations so as to adapt their behaviour to what the particular situation requires. We go on to describe the role metastability plays in learning of new skills, and in skilful behaviour more generally. Finally, drawing upon work in art, architecture and sports science, we develop a number of perspectives on how to investigate metastable attunement in real life situations.