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This article explores some implications of the counterfactual aspect of freedom and unfreedom. Because actions can be unprevented even if they are not undertaken, and conversely because actions can be prevented even if they are not attempted and are thus not overtly thwarted, any adequate account of negative liberty must ponder numerous counterfactual chains of events. Each person's freedom or unfreedom is affected not only by what others in fact do, but also by what they are disposed to do. Their dispositions play a key role in determining whether the abilities and inabilities of each person would continue as such if the person's conduct or situation were altered in various respects. Until one knows whether people would or would not have acted in certain ways if a given person had sought to do something, one cannot know whether that person was free to do that thing. Nor can one know whether the person was free to perform that action in combination with manifold subsequent actions. Thus, whether tacit or explicit, counterfactual scenarios are indispensable for any enquiry into a person's liberty. By relying (albeit perhaps only implicitly) on such scenarios, which trace how people are disposed to act vis-a-vis one another, one takes account of the central role of unmanifested dispositions in setting the bounds of people's sociopolitical freedom. Among the principal theorists whose work is critically examined in this article are Hillel Steiner, Ian Carter, and G.A. Cohen.