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Despite ample international literature regarding the school-to-prison pipeline, researchers in the Australian context have remained relatively silent about this phenomenon. While there are several studies investigating the criminological characteristics of juvenile detention in Australia, a substantial gap exists examining the educational exclusion of young First Nations males from the education system and whether this has a direct bearing on their overrepresentation in juvenile incarceration. Highlighted in this chapter are the cultural complexities and inequitable practices associated with high rates of exclusion of First Nations boys from school resulting in the likelihood of potential incarceration for some. Finally, certain pragmatic solutions are offered so that educators may reflect upon their important role in disrupting the school-to-prison pipeline.