The main objective of this study is to explore the nature of learning and the experiences of students involved in civic collective action, particularly during the 2011 Egyptian Revolution, and the role of Web 2.0 in the learning and collective action process. This study examines qualitative, in-depth interviews of five student activists in Egypt, and provides an interpretive analysis within and between participants. The study probes the participants’ conceptions of learning as they struggled against oppression, co-constructed new ways of understanding the world, and took collective actions to make political changes and achieve specific goals. Drawing on previous research and a broad spectrum of recent empirical developments, the study finds that the involvement in emancipatory struggle and social action, facilitated by Web 2.0 technologies, resulted in a transformational learning experience. That experience led to the acquisition of new knowledge and the development of new skills, which greatly enabled formerly voiceless students to break away from teacher-centered models of learning in Egypt, take control of their own learning, and consequently become autonomous thinkers ready for participation in a democratic society. Given the small sample size, the findings are limited to this study and are not suitable for statistical generalization, but the results are contextually transferrable to students in similar contexts in middle-eastern countries where teaching is still traditional and does not encourage critical thought. To apply the findings of this study more broadly, future research should explore similar instances in other countries, languages and cultural contexts.