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This research employs Weberian concepts of rationality to describe an environmental legal compliance process surrounding urban development in the US Rust Belt. Drawing on court records, official planning documents, and news media regarding the contested Kensington Expressway in Buffalo, New York, we explain how environmental legal compliance is defined in a local legal conflict. First, in its plan for the expressway’s redevelopment, the New York State Department of Transportation (NYSDOT) emphasized social and environmental outcomes to secure federal funding and neglected procedure to speed up the project. Second, community groups mobilized the law to challenge procedural flaws in the organization’s interpretation of compliance. Third, the court ruled that values cannot substitute for the rational procedures required by environmental regulations, deeming the plan noncompliant and irrational. These findings demonstrate that compliance is a socially emergent process and that conflicts arise when ambitious policies prioritize desirable ends over the technical means of achieving them.