Individuals sentenced to probation must follow a set of rules, or the conditions of probation. These conditions take effect immediately and require that individuals find and maintain employment and housing, stay within the boundaries of the local county, remain drug and alcohol-free, avoid bars and others with criminal histories, and abide by curfew hours. Importantly, these conditions do not account for the science of substance use disorders and recovery, do not consider the social structures in which individuals are situated, and do not consider how other social institutions (e.g. housing, employers) can get in the way of following these rules. As a result, individuals often find themselves breaking these rules, or collecting technical violations, for mostly legal behaviors and returning to jail. In response, two districts in Iowa have reconsidered their probation conditions. Specifically, one district reduced the number of conditions and the other district rewrote conditions to center change orientation. This presentation discusses the process the site took to change their conditions, the impacts of these changes on revocations and public safety, and offers a thorough discussion about how fewer rules may help probationers of all risk levels get across the finish line.