This study set out to explore the mechanisms for educating court-involved youth in Chicago, learn about the available educational options, and the barriers, if any, these young people face when continuing in or returning to school. A key finding is that educational options in Chicago that are designed expressly for court-involved youth who are not incarcerated or detained are limited to transitional programs that grant neither a high school diploma nor a GED certificate. As a result, youth who wish to complete secondary education are expected to attend schools that also are used by young people who are not involved with the court. Most of the individuals interviewed for this study believe that court-involved youth tend to be excluded from the regular public schools or that these schools are not a good fit for the needs of this population. The regular public schools are the only schools that have the capacity to absorb large numbers of youth and, other than the safe schools, they are the only schools available to youth under 16 years of age. If large numbers of court-involved youth do not enroll and finish their educations in the regular schools, they must compete with many other students for a limited number of seats in alternative programs. Some youth will find it difficult to gain entrance, particularly if they have severe academic deficits. To date, good data are lacking on educational outcomes for Chicago's court-involved youth. Although a few programs gather statistics on their own graduates, none follows students who enroll but drop out before completion, nor do any track program completers over the long term to determine if they continue (or resume) their education, obtain a diploma or degree, secure employment, or find themselves in court again. Finally, court-involved youth who do not enroll anywhere do not get tracked at all. Because it was intended as a preliminary exploration that would lay the groundwork for additional research, the present study's findings are more suggestive than conclusive, and much work remains to be done. What this work does do is lay out the programmatic and policy context with which court-involved youth in Chicago must grapple when seeking an education. At the same time, the findings raise concerns about the adequacy of available school options and the effect on school access of a broad range of educational policies and practices. Because education plays a such key role in youth development, it is critical that educators, and policy makers gain a better understanding of how well the educational system is working for those young people who already are struggling to be productive and successful. Research methods are described in the appendix. Questions for future research are detailed. (Contains 1 figure and 4 tables.) [This study was supported by a grant from Chapin Hall Center for Children's Research Development and Dissemination Fund.]