Criminals once traveled upriver to Sing Sing by boat from New York City, and the prison was built upon the rocky slope rising from the Hudson River. Located in present-day Ossining, housing has slowly become unaffordable on a correction officer’s salary. The new recruits, Conover’s classmates, have found shared housing in poor conditions. The cohort will spend the next four weeks on OJT, on-the-job training.

At the time, Sing Sing is being utilized in many ways as a training facility for new recruits. Thirty-four percent of officers have less than a year on the job, and there are upwards of seven-hundred-and-fifty security employees at the prison. Sing Sing is the second oldest prison after Auburn, and the second largest after Clinton.Sing Sing contains almost two-thousand inmates in maximum security and nearly six hundred in Tappan, the prison’s medium-security compound. There are about two-thousand violent felons, with around sixhundred imprisoned for murder or manslaughter. Fifty-six percent of inmates are black, thirty-two percent are Hispanic, and ten percent areCaucasian. There are few vocational programs, as almost all college-level programs had ceased in 1994 and 1995 due to federal lawmakers ending funding. Five inmates have committed suicide in five months, and the inmate-grievance system receives twenty-five grievances a week.