Parole laws, passed by most state legislatures at the turn of the century, provide for the release of prisoners before the expiration of their maximum sentence and for their supervision during their transition to free society. This article explores the early years of the parole system in Illinois. While the Illinois parole law indicated that parole agents would watch over ex-prisoners and aid in their rehabilitation, the state instead relied on private individuals, businesses, and voluntary organizations to supervise parolees. Agreements forged between prison officials and these supervisors illustrate the extent to which the private sector took on the functions of the state during the Progressive Era. As a result, employers and voluntary organizations developed a range of surveillance practices to maintain control over former prisoners, using informal systems of assessment and notions of success to evaluate the parolees in their charge. Though the parole system represented innovation on the part of the Illinois state government—a nod to emergent rehabilitative frameworks in penology—the reliance on voluntary organizations and businesses wove older class and gender ideals into this newer, purportedly more scientific and objective institution. This essay illuminates the everyday challenges of life on parole, tracing the experiences of ex-prisoners during the process of reentry and exposing the constant negotiations between employers, voluntary organizations, prisons, and parolees.