Little is known about the perceptions of teachers of their students returning from the juvenile justice system, which can influence student relationships and student engagement, both of which are critical to reduce recidivism rates. This study utilized an online survey to examine the perceptions of a convenience sample of 283 school personnel (e.g., special educators, administrators) from across the country on available transition services, school climate, self-efficacy, barriers faced during reentry, and supportive strategies. Findings indicate transition services are implemented inconsistently; personnel believe they have the ability to positively influence youth, yet they have low expectations for youth after graduation. Findings suggest opportunities for professional development on holding high expectations for youth, services to prevent negative outcomes. Implications for future research call for examination of wraparound services and analysis of transition services utilized across different states and regions of the country.