This chapter is, in many respects, an attempt to codify a series of questions that 1:1 schools have had to answer, whether they did so deliberately or on the fly. It is meant to prepare you for the many issues that you will face on the way to a successful 1:1 program. What it does not do is speak to the influential, authentic change you will see if your school does this well. When combined with a powerful change in pedagogical practice, a 1:1 computing program can help students and teachers create a learning environment that is truly transformative for all involved. The potential to create new ideas and solve problems when a digital device is in the hands of your students - along with access to the open-ended, accessible tools of Web 2.0 - can move schools from enclosed institutions surrounded by four walls to organizations at the forefront of deep and expansive learning.