This article explores the potential of digital technology to advance democratic citizenship. Drawing on critical theory and following a critical, comparative qualitative study which examined the relationships among digital technology, education, and democracy in the US and Israel, the authors explore epistemological assumptions of teaching and learning with digital tools. The article examines the tension between the promise of digital technology to transform education, and the instrumental hegemony of the neoliberal imperative. At the heart of this article, the authors contend that current teachers' understanding of using digital technology, and the practices used in classrooms constrain the promotion of digital citizenship. The authors argue that transforming education through digital technology and advancing civic aims require epistemological transformation which will move beyond instrumental understanding of digital tools. They conclude with a recommendation of a theoretical framework for digital citizenship.