Based on our research over the past ten years, we have identified six evidence-based transition practices that are critical for promoting youth success after release from secure care. Success, however, also relies heavily on the engagement of community partners and stakeholders who receive these youth after release. To further understand the construct of community engagement, we conducted a reintegration survey and held focus groups with stakeholders representing several agencies that provided services to youth from the juvenile justice system. We also interviewed youth to identify barriers in the transition process. The findings suggest that juvenile justice personnel need to consistently work in collaboration with community partners to generate and sustain the resources and awareness necessary to improve reentry outcomes for youth. Definitions of community engagement are offered and specific barriers and challenges that interfere with effective reentry are identified. Suggestions to improve reentry are included.