In this article, Peter Sipe compares his first year as a middle school teacher in Brooklyn, New York, to that of a rookie corrections officer at Sing Sing prison. Sipe explores what he considers to be disturbing similarities in these experiences, namely, a preoccupation with control, immersion in an adversarial social dynamic, and the prevalence of stress. Most ominously, Sipe suggests that both institutions share a legacy of failure. He posits that, just as prisons do not live up to their titles as "correctional facilities," his middle school does not produce educated children. (Contains 1 note.)