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Educational assessments, specifically standardized and normalized exams, owe most of their foundations to psychological test theory in psychometrics. While the theoretical assumptions of these practices are widespread and relatively uncontroversial in the testing community, there are at least two that are philosophically and mathematically suspect and have troubling implications in education. Assumption 1 is that repeated assessment measures that are calculated into an arithmetic mean are thought to represent some real stable, quantitative psychological trait or ability plus some error. Assumption 2 is that aggregated, group-level educational data collected from assessments can then be interpreted to make inferences about a given individual person over time without explicit justification. It is argued that the former assumption cannot be taken for granted; it is also argued that, while it is typically attributed to 20th century thought, the assumption in a rigorous form can be traced back at least to the 1830s via an unattractive Platonistic statistical thesis offered by one of the founders of the social sciences—Belgian mathematician Adolphe Quetelet (1796–1874). While contemporary research has moved away from using his work directly, it is demonstrated that cognitive psychology is still facing the preservation of assumption 1, which is becoming increasingly challenged by current paradigms that pitch human cognition as a dynamical, complex system. However, how to deal with assumption 1 and whether it is broadly justified is left as an open question. It is then argued that assumption 2 is only justified by assessments having ergodic properties, which is a criterion rarely met in education; specifically, some forms of normalized standardized exams are intrinsically non-ergodic and should be thought of as invalid assessments for saying much about individual students and their capability. The article closes with a call for the introduction of dynamical mathematics into educational assessment at a conceptual level (e.g., through Bayesian networks), the critical analysis of several key psychological testing assumptions, and the introduction of dynamical language into philosophical discourse. Each of these prima facie distinct areas ought to inform each other more closely in educational studies. Full article