The primary purpose of this investigation was to examine the effects of a program designed to improve adolescents' relationships with at least one teacher in an urban high school. All participating students were nominated by teachers as having significant emotional and behavioral problems and approximately half of these youth were randomly assigned to an intervention that included increased positive involvement between each student and one teacher within the school. Teacher ratings of students' social, behavioral, emotional, and academic adjustment at pre- and post-intervention indicated that students in the intervention group had higher grade point averages than did students in the control group following the 5-month intervention but no differences were observed on other variables. Challenges associated with conducting school-based, relationship-focused interventions in high-poverty urban environments and several lessons that were learned in the process of initiating this project are discussed.