Background: In the debate about how to evaluate students suspected of having a learning disability, the role of context in learning has been consistently minimized in the United States. Objective: This article explores the implications of the current, deficit-based approach to the definition and assessment of learning disabilities and offers a more contextually and culturally responsive alternative. Methods: An examination of the epistemic foundation and the implicit assumptions that underpin current practices reveal the need for a contextualized approach to evaluate individuals that takes into account the interactive roles of the environment and the individual. Results: Decontextualized methods of learning disabilities assessment have negative consequences for many students and contribute to the disproportionate representation of culturally and linguistically diverse students in special education services. This article describes a contextualized approach rooted in a model of ecological congruence that characterizes a student's educational experiences and outcomes as a result of a dynamic process between the student and the classroom environment. Conclusion: Contextual and culturally responsive approaches to evaluation such as ecological congruence can provide a richer and more accurate view of how to remove barriers that impede academic progress.