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The authors interrogated the contextual spectra of educational and sociological literature to highlight the failings of the No Child Left Behind Act of 2001. Historical and contemporary perspectives on the state of urban schooling, school choice, and community identify fundamental areas in which disadvantaged students are affected disproportionately. Additionally, treatment of the TRIO programs (Upward Bound and Talent Search) and their positive impact on disadvantaged students is presented. The TRIO programs consider issues germane to the academic achievement of low-income, disadvantaged, and marginalized students in ways that the No Child Left Behind framework fails to consider. Policymakers, K-12 teachers/leaders, and parents are admonished to pay careful attention to how No Child Left Behind continues to leave underprivileged children behind through ignorance of their communities and disparate accountability measures. Implications for policy are discussed.