In response to the overrepresentation of Native Hawaiian and Pacific Islander individuals incarcerated in Hawai’i and numerous legislative task force recommendations, the University of Hawai’i Community Design Center developed a Cultural Competence Framework for correctional planning and design in partnership with the State of Hawai’i Department of Public Safety. This chapter describes the academic, outreach, and research efforts that informed the development of this framework and toolkit, which include six tools that take a “small bets” approach to the transformation of institutional systems, knowledge, practices, and spaces. The tools are offered as a collection of culturally aligned, place-based, and community-engaged approaches and resources critical to creating more just institutional processes and environments applicable to both teaching and practice.