Freedom can be seen as individual’s capacity to choose between alternatives. As such, it stands in a dialectical relationship to its environment that both imposes constraints on freedom and allows carrying it out. Yet if we see liberty as freedom’s social accommodation, how would freedom shape liberty, and how would liberty accommodate freedom? As a capacity for choice, freedom is formal. Negative liberty, or freedom from, protects this capacity yet does not give it content. To make freedom meaningful, its societal accommodation has ensure that the choice can be carried out – in terms of accessing alternatives, understand them, and making informed choices. The paper, using the tools provided by the Hegelian philosophy and by information theory, explores the concept of liberty as an enabler of freedom and the role of knowledge in its enablement. This exploration leads us to specific positive rights that are necessary to make freedom meaningful.