Background/Context: In most judicial and social science debates about school desegregation, it is usually assumed that educational and social benefits, if significant, help establish a compelling purpose for school desegregation plans. Less thought has been given to whether the degree of benefits should factor into whether a plan is narrowly tailored according to Supreme Court standards. Hence, many were surprised when Justice Kennedy argued in the Seattle case that school desegregation meets the compelling purpose requirement but that desegregation plans that classified and assigned all students on the basis of race violated the narrow tailoring requirement. Purpose/Objective/Research Question/Focus of the Study: The essay offers a social science rationale for Justice Kennedy's views about narrow tailoring issues and suggests several approaches to desegregation plans that may meet narrow tailoring requirements in the future. Setting: For illustrative purposes, the study uses student achievement data from Charlotte-Mecklenburg, North Carolina, between 2001 and 2006. The data were obtained from the North Carolina Education Research Data Center at Duke University. Population/Participants/Subjects: From a larger North Carolina data set, a cohort was drawn consisting of about 4,050 Black students from the Charlotte-Mecklenburg district who began third grade in 2000-2001 and completed the eighth grade in 2005-2006. Research Design: This essay is primarily an analytic essay with a brief quantitative analysis of student achievement data. Data Collection and Analysis: The quantitative analysis of achievement data utilized longitudinal methods, tracking socioeconomic-status-adjusted achievement trends for Black students over time. Findings/Results: A modest relationship between school desegregation and Black student achievement (0.2 standard deviations over 5 years) masks a substantial overlap in test scores for individual students in desegregated versus segregated schools. That is, many Black students in segregated schools score higher than the typical desegregated Black student, and vice versa. Conclusions/Recommendations: Using evidence from within social science, the authors find that the current design of most mandatory desegregation plans does not fit within the current Court's (especially Justice Kennedy's) view of narrowly tailored plans. However, there are several ways in which school boards and other policy makers can promote school desegregation: considering race when drawing attendance zones, building new schools, closing schools, and locating magnet schools in strategic areas. Further, magnet schools might meet narrow tailoring requirements if race is only one of several factors considered during the application and administration process.