Individual differences in trajectories of anxious withdrawal were examined from Grades 5 to 8 across the transition to middle school in a community sample (N = 283), using General Growth Mixture Modeling. Three distinct pathways of anxious withdrawal were identified: "low-stable" (78%), "high-decreasing" (12%), and "high-increasing" (10%). In Grade 6, relative to the low-stable class, greater peer exclusion and more free time spent with mother predicted membership in the "high-decreasing" class; higher peer exclusion predicted membership in the "high-increasing" class. Within the "high-increasing" class, the growth of anxious withdrawal was predicted by lower parental autonomy-granting, less free time with mother, both nurturing and restrictive parenting, and greater peer exclusion. Results highlight the role of both parent-child relationship and peer difficulties in increasing the adjustment risk among youth who are anxiously withdrawn prior to the middle-school transition. (Contains 4 tables and 1 figure.)