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Scholarship on Latinos’ lagging US high school graduation and college enrollment rates has focused on systematic biases and inequities in schooling. This article argues for an additional complementary explanation for underachievement and school failure. Namely, it suggests that high school underachievement in Latino children of immigrants can be attributed in part to the bureaucratic nature of schooling and a constant onslaught of bureaucratic errors and omissions. Based upon a 5-year multiple-case study in the southeastern United States, it finds that bureaucratic dysfunctions figured prominently in the education of Latino immigrant youth. The article calls for more research on the impact of bureaucratic errors on educational paths of immigrant students and argues that educators might profitably draw from work on organizational failure to help Latino children of immigrants navigate school bureaucracies more successfully.