Taking the “right to disconnect” discussion as a starting point, this article considers how the im/possibility of “opting out” is ruminated in scholarly discourses on technology non-use, media resistance, and media disruption. I argue that while very different in scope, these discourses converge in that they all revolve around a structuring paradox. On one hand, this paradox is set in place by the paradox of dis/connectivity itself (no disconnectivity without connectivity). On the other hand, I argue, it is incited and reinforced by the use of scholarly methods that appear to be at odds with the gesture of disconnectivity itself, whether they be empirical, discursive, or technical (or legislative). This article stakes a claim for the importance looking at these discourses on dis/connectivity from the point of view of this structuring paradox, for it is here, I argue, that the limits of our current “culture of connectivity” are most forcefully negotiated.