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This study provides new insight into the assessment of the standardized achievement outcomes of those retained students in their postretained years. To do so, this evaluation employed a longitudinal sample of entire cohorts of urban elementary school children in the Philadelphia School District over six years of observations. For the approximate 21% of students retained in the sample, the analyses on postretention performance were conducted on a same-age sample. The results demonstrate that a measure of grade retention per se is not a statistically significant predictor or achievement. Rather, as retained students are placed in classrooms with higher average and greater standard deviation in peer ability, they tend to achieve lower test performance in their postretention years. Implications are discussed.