We studied the transition from elementary to middle school for 74 fifth-grade students. Specifically, we examined how behavioral risk evident in the elementary years, as measured by the Student Risk Screening Scale (SRSS), impacts students transitioning from elementary to middle school. First, we examined how student risk status shifts as students transitioned from elementary to middle school, also exploring whether these shifts in risk were comparable with the shifts in risk occurring within the fifth-grade year. Second, we explored the degree to which these shifts in risk varied as a function of student gender, special education status, and initial behavioral performance. Although gender was not predictive of performance, there was a positive relation between special education status and initial behavioral risk when compared with risk evident during the sixth-grade year. Finally, we determined the extent to which risk at the end of elementary school was associated with academic and behavioral performance during the first year of middle school. Findings suggest a strong relation between grade point average (GPA) and course failures (CFs) with behavioral risk in sixth grade. As expected, there was a statistically significant, positive relation between CFs and sixth-grade SRSS scores and an inverse relation with GPA.