Digital technologies are increasingly personal, mobile, and connected. Many students use them in their daily lives, but in schools they are regularly limited in what tools they can use and what digital content they have access to. While students want to use digital technologies for learning, educators often ban or limit this use for reasons of safety or learning distractions. This chapter explores the divide between teachers and students, the technologies that could increase the size of this gap, and what educators need to reconnect teachers and students, and education and life. Personal, mobile, and connected technologies should be seriously considered as learning tools, as they can provide the bridge between schools and their surrounding communities, reconnecting the two with learning that is relevant, meaningful, and lifelong.