The present study investigated longitudinal associations between behavioral and cognitive dimensions of parental social coaching (i.e., advice about how to behave or think about peer challenges) and young adolescents’ peer acceptance, and whether such associations are moderated by youths’ social skills. Time 1 (T1) participants included 123 young adolescents (M age = 12.03 years; 50% boys; 58.5% European American). Parents gave open-ended reports about their social coaching to hypothetical peer stress scenarios, which were coded from low to high quality on behavioral and cognitive dimensions. Parents and teachers reported on adolescent prosocial behavior (i.e., social–behavioral skills), and adolescents reported on their social appraisals and social self-efficacy (i.e., social–cognitive skills). At T1 (before the first year of middle school) and Time 2 (approximately 10 months later, after the first year of middle school), parents and teachers rated adolescent peer acceptance. Analyses revealed that parents’ prosocial behavioral advice and benign cognitive framing independently predicted adolescents’ higher peer acceptance prospectively (controlling for earlier levels of peer acceptance). Furthermore, adolescent social skills moderated links between coaching and peer acceptance. Specifically, adolescents with higher, but not lower, social–cognitive skills became more accepted in the context of higher-quality coaching, supporting a “capitalization” pattern, such that these youth may be better able to utilize coaching suggestions. Results underscore the utility of parents’ behavioral advice and cognitive framing for adolescent peer adjustment across the middle school transition and suggest that optimal social-coaching strategies may depend in part on adolescent social skill level.