In this chapter, attention again turns to issues surrounding freedom. In chapter two it was argued that the dual power to do otherwise, to be able to A and to refrain from A-ing, was a necessary condition of a concept of freedom, which was named ‘regulative freedom’. In this chapter, a contextualist analysis of regulative freedom is proposed. The chapter begins by considering different possible formulations of a contextualist account of freedom, after which, semantic evidence both for and against the view is examined. Next, two significant advantages of the contextualist theory are outlined, namely, a response to the (reformulated) consequence argument and the argument from manipulation. Finally, objections to a contextualist account of regulative freedom are answered.