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While many research and policy proposals offer solutions to remedy a failing justice system, the operational requirements and “real politick” necessary to implement these and affect change are complex. This paper examines several large-scale justice policy proposals to identify some challenges in translating these policies into practice. It addresses the pitfall of looking through a prescriptive lens when approaching a complex policy issue. For example, reducing jail populations by providing more community-based or reentry services is one that involves public safety officials, the culture of justice institutions, and the capacity of community-based providers to effectively treat short- and long-term needs and coordinate with one another. Additionally, structural and long-lasting transformation requires smart investments in strategies that robustly demonstrate the ability to provide benefits as well as cost savings. Conducting cost-benefit analysis is important for upfront funding and sustainability. Finally, the political will required for justice transformation cannot happen without public support, so framing the political discourse in a way that taxpayers and residents understand the benefits of reforming the justice system is as essential as having a political, fiscal and substantive reform strategy.