Improvisation, understood as a skillful activity, suggests a tension between the constitutive roles of habit and creativity. Cognitive and phenomenological accounts of skill acquisition point to the importance of developing habitual responses that facilitate fluid performance. Yet, habit formation is associated with repetitive behavior. Seemingly at odds with repetition, spontaneous invention is often regarded as the basis of improvising creatively. The puzzle – how habit and creativity relate in skillful improvisation – is resolved by drawing on a view of the brain as an embodied, predictive organ, entangled in cultural scaffolding, and perpetually engaged in inference. This view is in part rooted in the pragmatist tradition, as is a large body of work on music. By combining these strands of theoretical and empirical research, an account of action-oriented abduction is developed and applied to an illustrative vignette. The resulting application goes beyond existing accounts to articulate an enriched sense of creative improvisation.