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In the United States, Black preschoolers are suspended at disproportionately high rates when compared to other groups. This chapter examines the causes behind the so-called “school-to-prison pipeline,” including the psychological predilection to not label a Black child’s behavior as “bad” but to label the child that way. We offer a personal narrative to ground our research in an approachable, anecdotal fashion in an attempt to remind researchers, policymakers, and educators that this is not just about statistics, although those are included as well. However, behind every statistic is a real child with a real family who is plagued by this pipeline. Furthermore, the personal narrative also sheds light on the overwhelming pressure and stress that simply comes from being Black, and raising Black children, in an America dismissively considered “post-racial.” Finally, and importantly, this chapter explores ways in which changes can help prevent the exploding Black prison population and investigates ways in which that change can functionally take place. It is not enough to acknowledge an ongoing injustice is occurring; we must fix it, no matter how uncomfortable that fix is or how challenging.