This study examines several aspects of adolescents’ pretransition peer relationships as predictors of their adjustment to middle school. Participants were 365 students (175 boys; 99% Caucasian) involved in the Time 1 (the spring of fifth grade) and Time 2 (the fall of sixth grade) assessments. Adolescents completed measures that assessed peer acceptance, number of friends, the quality of a specific mutual friendship, loneliness, depression, self-esteem, and involvement in school. Academic achievement and absentee data were obtained from student files. Regression analyses indicated that the pretransition peer variables predicted posttransition loneliness, self-esteem, school involvement, and academic achievement. The patterns of prediction varied slightly for each adjustment variable, with the most robust relationship being between peer acceptance and achievement. Results of repeated-measures MANOVAs indicated no differential changes in adjustment across time by gender. Implications for including a peer component in programs that prepare students for the middle school transition are discussed.