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Probation conditions are a longstanding part of community supervision, monitoring clients’ behavior and potentially promoting their successful (re)integration into society. This study examines the appropriateness of probation conditions from the perspective of probation officers, focusing on how well these conditions address the criminogenic needs and risk factors of various populations. In this context, appropriateness refers to the adequacy of a condition to address a client's risk and/or need factors—a critical aspect in evaluating the effectiveness of probation conditions. The study is based on 72 in-depth interviews with 94 probation officers from a large statewide U.S. probation agency. Findings reveal that officers identify several reasons why conditions may become inappropriate in certain situations, including mismatched conditions that do not align with the individual's risk/need factors, unachievable conditions that individuals cannot comply with due to factors outside their control, and duplicative conditions that overlap with other conditions or laws that everyone must abide by. Viewed through the lens of the Risk-Need-Responsivity (RNR) model, these challenges highlight potential disruptions in aligning probation conditions with clients' risks and needs. The findings help inform policy adjustments aimed at enhancing the effectiveness of probation conditions, with possible implications for both rehabilitation outcomes and community safety.