There is consensus among scholars, policy experts, and ordinary Latinos that a Latino education crisis exists, and that education is the primary vehicle for achieving the American Dream. Yet we know surprisingly little about what predicts Latinos’ views of the bureaucrats and organizations charged with translating their educational hopes into reality. This study links disparate literatures to provide theory and evidence about how group features and elements of citizen-bureaucracy relations explain Latinos’ judgments of schools and their assessments of contact with school officials. Using the 2006 Latino National Survey, we find that nativity, acculturation, and discrimination undermine positive evaluations. Our results also indicate that some of these negative associations might be countered with Latino-salient outreach, including providing school-relevant information in Spanish language.