Using administrative data on public school students in North Carolina, we find that sixth grade students attending middle schools are much more likely to be cited for discipline problems than those attending elementary school. That difference remains after adjusting for the socioeconomic and demographic characteristics of the students and their schools. Furthermore, the higher infraction rates recorded by sixth graders who are placed in middle school persist at least through ninth grade. An analysis of end-of-grade test scores provides complementary findings. A plausible explanation is that sixth graders are at an especially impressionable age; in middle school, the exposure to older peers and the relative freedom from supervision have deleterious consequences. These findings are relevant to the current debate over the best school configuration for incorporating the middle grades. Based on our results, we suggest that there is a strong argument for separating sixth graders from older adolescents. © 2008 by the Association for Public Policy Analysis and Management.