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Research that tracks low-income populations across educational transitions contains threats to validity that can compromise evidence-based educational policy and practice. The Big Picture Longitudinal Study is a national, multiyear study that follows low-income urban youth who were accepted into college as high school seniors. Triangulating the results of multiple longitudinal data sources showed that reported college aspirations and enrollment intentions were inconsistently and differently reported by students and teachers in the final semester of high school. Relying on a particular data source and time can result in mistakenly equating college aspirations and enrollment behaviors, these findings suggest. In particular, secondary school educators’ inflated assumptions about their students’ college aspirations can obscure the need for supporting multiple pathways to college and work for low-income, first-generation high school seniors.