The concept of freedom is one of the key ideas in political philosophy. In a liberal society one can do, live, and like whatever he/she pleases, but at the same time there are certain constraints on the individual that balance between one's desires and the common good. In this paper, the author examines the notion of freedom in the age of digital technology, and argues that attaining freedom requires reconsidering the traditional liberal distinction between "negative" and "positive freedom." The author introduces the distinction between the two concepts of freedom, discusses Dewey's notion of freedom, and examines freedom, technology, and the quest for democracy. This paper argues that rather than focusing on mechanisms of control and limiting digital freedom, educators should foster students' critical literacy of digital technology and provide them learning environments that enable the development of social responsibility capacities and active citizenship.