As friends increase in closeness and influence during adolescence, some friends may become overprotective, or excessively and intrusively protective. Engaging in overprotective behavior, and being the recipient of such behavior, may have positive and negative adjustment trade-offs. The current study examines, for the first time, bidirectional associations between friend overprotection and several adjustment trade-offs, including internalizing problems (i.e., depressive and anxiety symptoms), peer difficulties (i.e., rejection and physical and relational victimization), and positive friendship quality (i.e., closeness, help, and security) during early adolescence. Participants were 269 young adolescents (140 boys; M = 11.46, SD = 0.41) who completed self-report and peer nomination measures in their schools at two time points 4 months apart (Fall and Spring of the school year). Structural equation models revealed that being overprotected by a friend predicted decreases in friendship quality and was predicted by peer difficulties and internalizing problems (negatively). Being overprotective of friends predicted increases in internalizing symptoms and was predicted by peer difficulties. Findings are novel as they suggest that friend overprotection may be risky (and not beneficial) for both the overprotector and the overprotectee, setting the stage for future inquiry in this new area of peer relations research.