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The present study examines probation conditions from the perspective of probation staff to understand how they perceive the ability to monitor and oversee conditions of supervision. Researchers conducted 72 in-depth interviews with 94 probation officers in the Massachusetts Probation Service. The concept of enforceability appears to influence the officers' perception of useful, appropriate, or meaningful conditions of supervision. The study outlines various conditions such as GPS monitoring or drug/alcohol-free requirements and the circumstances that officers perceived to make the condition unenforceable. The findings provide valuable insights that can inform policy adjustments and improvements to enhance the effectiveness and contribution of probation conditions to community safety.