Following a series of transformative political and legal battles, California's overcrowded prison system has moved in the direction of moderate decarceration. A softer stance on punishment means that thousands of previously ineligible inmates serving indeterminate sentences are now being considered for release on parole. Drawing on ethnographic observations of twenty parole hearings in one California men's prison, this study outlines how rehabilitation has come to be enmeshed in a logic of punitivity, as parole commissioners subject inmates to an individualizing gaze that misrecognizes the socially embedded nature of their performance. Parole commissioners are tasked with assessing dangerousness, deploying a multifaceted conception of risk that combines formalized actuarial instruments and evaluative judgments to form the inchoate and contradictory notion of “insight.” Inmates are expected to demonstrate this if they are to be released, but what is insight? Parole boards assume that it is a valid indicator of future behavior and probable recidivism, and parole commissioners posit that successful inmates will be capable of demonstrating authentic remorse and insight, unimpeded by the constraints of an austere and dangerous carceral environment. However, the discretionary criteria established by the penal system are limited by the deleterious living conditions established by this same penal system.