["Criminology, Volume 60, Issue 1, Page 27-59, February 2022. ", "\nAbstract\nThis article explores one way prior punishments may contribute to cumulative disadvantage: through more severe sentencing of those under criminal justice supervision. We examine the impact of being on supervision in Michigan on receiving a sentence of imprisonment—comparing the magnitude of the impact reflected in the formal sentencing guideline recommendation with deviations made by court actors. We find that the formal penalty for supervision status is modest, whereas court actors place substantially more weight on current parole status than do the guidelines when deciding to sentence a defendant to prison. They do not seem to give current probation status extra weight in a consistent way. As such, parole is more likely to contribute to cumulative disadvantage stemming from prior punishments. This disproportionately impacts Black defendants because of their higher rates of parole—not through disproportionate sentencing conditional on parole status. Findings suggest that attempts to address factors contributing to cumulative disadvantage will need to consider not only formal rules but also how informal discretion contributes to prison sentences.\n"]