Skill acquisition represents a progression from high to low reliance on the conscious control of the action. The ability to produce action without drawing upon limited attentional resources has traditionally been the defining characteristic of skill automaticity. As such, learning represents a progression from low to high efficiency in the cognitive processes needed to plan, execute, and update skilled movement. In this chapter, we summarize neuroimaging findings that illustrate the evolution of such efficiency in terms of the neural adaptations that underlie skill learning automatization. As a backdrop to these findings, we first review the cognitive characteristics of skill automaticity as well as a contemporary theoretical framework for how we perform action based on sequencing movement elements. This provides a vantage point from which neural basis of skill automaticity can be considered in terms of associative and sensorimotor learning processes that provide for more efficient action in terms of cognitive requirements. We then contrast this with a summary of the contextual interference effect, which represents a cautionary account for the negative learning consequences associated with training protocols that appear to expedite skill automaticity.