From 2010 to 2015, the Arts Infusion Initiative helped expose, inspire, and connect detained youth and those at risk of incarceration to rigorous and engaging arts instruction, infused with social and emotional learning goals. Funded by the Chicago Community Trust, this $2.5 million demonstration earned collaboration from the local detention facility, public school system, community policing office, and community arts program leaders. This research describes findings and recommendations from the Urban Institute’s mixed-method evaluation of the Arts Infusion Initiative, commissioned by the National Guild for Community Arts Education with funding from the Chicago Community Trust.