This paper reports the results of a four year study of a project designed to bring the Internet to a large urban school district with the explicit purpose of breaking down barriers between the schools and the outside world. The study was conducted using qualitative research methods including extensive observation in classrooms and other sites, the conduct of over 200 interviews with administrators, teachers, students, and the collection of a wide variety~ of archival materials. Data were analyzed using established methods [1, 2]. Use of the Internet made possible a substantial amount of contact between students and the outside world. However, problems arose that prevented students from using the Internet as readily and productively as originally envisioned. These problems can be conceptualized as flowing from mismatches in schedules, goals, and norms either between the schools and the outside world or inside of the schools.