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The purpose of the study is to examine the complex relationship between Juvenile Detention Officers and the youth that are detained at juvenile detention centers, specifically at the McLean County Juvenile Detention Center, in Illinois. The research problem of this study is the aspects of working with justice-involved youth that lead to complex relationships. This study will be conducted through covert research. It was found that the barriers that restrict meaningful rehabilitation efforts for justice-involved youth may be contributing to recidivism and repeated incarceration, which can complicate youths’ relationships with juvenile detention staff that may be invested in the success of the youth. This lack of rehabilitation was not observed to complicate the relationships of all juvenile detention workers, possibly due to preconceived personal beliefs of justice-involved youth. In conclusion, the lack of resources available to justice-involved youth that could reduce recidivism complicates relationships with juvenile detention staff who hope to help the juveniles they work with in a meaningful way, which leads to frustration among juvenile detention staff that is expressed in a variety of manners.