Youth transitioning out of the juvenile justice and foster care systems face many challenges, one of which is securing housing. Unfortunately, programs around the country created to address these challenges often do not use an integrated holistic approach, leaving youth at risk of an unsuccessful transition to independence. This study assesses the Bridging the Gap intervention which integrates housing services and an independent living coach (ILC) to address the instrumental and relational support needs during the youth’s transition. This study uses mixed methods to deeply understand the needs of youth transitioning out of juvenile justice and foster care systems and to assess correlates of a successful transition. Qualitative and quantitative results confirm that youth transitioning our of juvenile justice and foster care systems face a wide range of challenges. Results also show that only a participant’s age is correlated with a successful transition. Findings from the study can be used to inform other programs addressing both the instrumental and relationship support needs of youth transitioning out of foster care and corrections.