Historically, Iowa’s Department of Corrections, and many probation agencies across the country, have relied on numerous probation conditions, or the set of rules, to provide structure and guidance for individuals under supervision. Yet, recent research shows many individuals struggle to follow these rules because there are often too many rules, the rules do not offer flexibility to a population with few resources to comply with them, and the rules do not align with the research on behavioral change. Too often, then, individuals return to jail, for breaking these rules—coined, “technical violations.” Across many jurisdictions these technical violations are the primary driver to returning to jail—not new crimes.