This chapter explores the moral and psychological dimensions of the neo-Roman concept of freedom, dimensions that have often been overlooked in favour of a political (and, still more narrowly, republican) analysis of non-domination. Through the example of Montaigne, the late sixteenth-century moral essayist, I argue that neo-Roman freedom is neither exclusively nor intrinsically republican in orientation, that it is best understood as a claim about the status of persons, and that this approach provides a firmer basis for establishing its distinctiveness and value than those accounts, including Quentin Skinner’s, which cast it as a robust variant of non-interference.