Based on qualitative research conducted from 1998 to 2001, this article describes classroom interactions in a high school and examines two uses of rules: one associated with confinement, and another associated with cognitive skills development. Though the two forms overlapped, the first was more prevalent in self-contained classes, and the second in the general education classes. At one level, the article describes how rules are part of an interaction between teachers and students, in which both groups are active in using rules to obtain benefits relating to personal fulfillment, peer approval, and social positioning. At another level, the article discusses how rules are used to teach some youths individual responsibility and respect for authority (preparing them to be law-abiding citizens and professionals in a world where they will have choices and some level of free will), while others, who are predominately African American, Latino, male, and poor, are literally surrounded by rules and placed in classroom arrangements that prepare them for immobility and limited choices. The uses of rules are examined in relation to social and economic realities involving work and the preparation of youths for a global economy, and for the way that school becomes a provider of free wills, offering mobility and choice for some, and confinement for others.