This essay is part of a symposium on Julie Cohen’s book, Configuring the Networked Self: Law, Code, and the Play of Everyday Practice (Yale University Press 2012). It discusses a central idea in Cohen’s theory: semantic discontinuity. “Semantic discontinuity” means gaps, flexibilities, and inconsistencies in systems of digital control. As we build digital systems to achieve our goals – for example, social order, national security, or property protection – we generate an increasingly complicated amalgam of practices, norms, and technologies of control. And as those practices, norms and technologies become increasingly powerful and pervasive, they may do more than protect our rights; they may actually decrease our practical freedom. An imperfect system of control, rather than being a hindrance to human liberty, may sometimes be necessary to it, even if this means that some violations of the law will go unpunished and some norms will be only imperfectly realized. As techniques of surveillance, governance, and control multiply and overlap in modern societies, gaps and imperfections in these systems – some designed, and some accidental – become increasingly important. That is because they allow room for maneuver and space for improvisation. Cohen’s concept of semantic discontinuity is not a complete account of human freedom. It is merely one aspect of what freedom might mean in a networked world, along with (for example) other values like access to knowledge and effective transparency. The essay discuses the strengths and weaknesses of semantic discontinuity as a theory of digital freedom. I conclude by applying Cohen’s ideas to the problems of freedom of speech in the digital world. Cohen’s account has important parallels to my own theory of democratic culture. Moreover, her idea of semantic discontinuity has interesting analogies in free speech doctrine; two examples are immunities for digital intermediaries and the rule against prior restraints.