The revolving door of the prison system may be the most persistent challenge faced by criminological practitioners and scholars. Following reentry from custody, the majority of former prisoners end up back in the system within three years, suggesting that correctional involvement is not an isolated incident for most offenders. Through its analysis of parole violations and sanctions, this dissertation project offers important new insights on the “revolving door” process. The report includes: 1) Three empirical chapters on the phases of recidivism: offending behavior, institutional responses to offending behavior, and the consequences of institutional sanctions on offender well-being. And, 2) three analytical chapters on: the geographical proximity to social service providers and how it relates to recidivism; how “supervision regimes” (the legal, political, and cultural factors that shape supervision) influence recidivism; and of the causal impact of how short-term custody interferes with the ability of parolees to find and maintain work. Findings suggest that: a) the observed impact of contextual conditions on recidivism depend on how expansively one defines the “community” in which parolees are embedded and further demonstrates the importance of capturing the effect of service accessibility on offending behavior within the larger ecological context of where parolees live; b) that regional and county-level attributes shape local templates for decision-making among parole officers in ways that affect not only whether parolees are revoked to prison, but also the use of alternative sanctions, such as stricter community supervision and incarceration in short-term correctional facilities such as jails or detention centers; and c) the experience of short-term re-incarceration dramatically increases the risk of unemployment among parolees in the months during and following their incarceration.