Using data from a longitudinal study of high-risk children (N = 174), the authors examined deflections from predicted achievement scores on the basis of the discrepancy of observed scores from an established regression line (from first to sixth grade and first grade to age 16 years). Years in special education and socioeconomic status (SES) were related to changes in math achievement between first and sixth grade, whereas SES, child behavior problems, and quality of home environment were related to deflections in achievement from first grade to age 16 years. The environmental factors, quality of home environment, parent involvement in the child's education, and SES were related to improved achievement across time. These results suggest that early school, family, home environment, and child factors are important predictors of academic achievement deflections in late elementary and high school.