Justice-involved youth have a high risk of reoffending after release, indicating the need for evidence-based reentry programming. This paper presents the results of a two-year post-release non-randomized comparison study. The study examined the impact of enhanced transition programming, delivered through Reentry Intervention and Support for Engagement by Integrating Technology (RISE-IT), on recidivism by comparing two groups, youth who received enhanced vs. traditional transition services in a secure care facility. Enhanced services included: enhanced reception, assessment & classification, transition planning, vocational preparation, merging two worlds curriculum, and 30-day aftercare support. Results indicate that youth who received enhanced services through RISE-IT had significantly lower rates of recidivism. Limitations and implications for practice, as well as future research, are discussed.