Adolescents becoming formally involved with a juvenile court because of school-related behavior and discipline problems is a phenomenon known as the school-to-prison pipeline. Adolescents with learning disabilities are disproportionately represented within this pipeline. A study was conducted to review the outcomes for a population of youthful offenders (n = 433) in two juvenile courts in the Midwest, and it was found that youthful offenders with learning disabilities, when compared with nondisabled youthful offenders, were more likely to be suspended from school, were adjudicated delinquent at younger ages, and were more frequently held in detention centers. These outcomes are all risk factors for ongoing delinquent behaviors and, for some, eventual adult criminal court involvement. It is recommended that the juvenile courts continue to shift toward a rehabilitative paradigm in working with this more vulnerable offender population, including increased use of social workers.