Roughly one-third of the people under the purview of the Rhode Island Department of Corrections are on active probation. People on probation are typically mandated to a variety of stipulations, such as meetings with their probation officer, court appointments, drug and/or mental health counseling, and crime-specific stipulations, such as anger management groups. Evidence suggesting that mandating these stipulations reduces a person’s likelihood to be rearrested is minimal. In contrast, there is a wealth of evidence suggesting that stable employment decreases recidivism. A person’s perceptions of their employability have been demonstrated as a key component to both pursuing and maintaining employment opportunities. Drawing on Labeling Theory, this study surveyed 170 persons on active probation to explore the correlation between probation stipulations and employability perceptions. Results suggest there is a negative association between stipulations and perceptions of employability. Social work practitioners working with people on probation or people who are incarcerated should work to increase their clients’ perceptions of employability.