Many practitioners are looking for ways to bring the vitality of Mobile 2.0—for example, social networking via a mobile phone (cellphone), or photo sharing on a mobile blog—into formal learning and teaching. But they face a complex and even paradoxical challenge: how can they harness that vitality without stifling its most distinctive feature—the fact that it is user led? This chapter begins with an analysis of that paradox as a foundation for understanding the challenges that practitioners face now and in the future. Drawing on data from interviews with six experienced tertiary practitioners, the authors describe and analyze a number of examples that point to the particular power of mobile devices to blur formal and informal activity in people’s lives. The aim is to look beyond the hype around innovations in mobile devices and connectivity to focus on the opportunities for practitioners to bend the arc of Mobile 2.0 to the needs of their learners.