Background: Adolescents who begin high school with a poor record of academic performance are often at risk for developing maladaptive academic behaviors, which can impede academic success in the long run. Objective: Guided by the substantial literature on the academic and motivational benefits of adolescents' conversations, this study examined the differential effects of having conversations with different socializers. This study aims to identify consolidated and generalizable effects of various sources of support in adolescent lives and contribute to educational practice for adolescent academic adaptation by examining multiple types of socializers using a large nationally representative sample. Methods: Adolescents' conversations about course-taking and personal issues with mothers, fathers, teachers, friends, and school counselors were examined for their potential buffering roles in the relationship between GPA and maladaptive academic behaviors. Data from 22,940 students (49.22% female, 9th through 11th-grade) in 690 U.S. schools from the High School Longitudinal Study of 2009 (HSLS:09) were analyzed using multiple regression analyses that incorporated longitudinal sampling weights and adjusted for clustering within schools. Results: Conversations with friends about personal issues during the 9th-grade year predicted greater subsequent maladaptive academic behavior. Students with lower 9th-grade GPAs were more likely to utilize maladaptive academic behaviors during the 11th-grade. This association, however, was less strong when students had conversations about either course-taking or personal issues with their teachers. Conclusion: Adolescent-teacher conversations about academic and personal issues can buffer against the development of maladaptive academic behaviors during high school, particularly for students who are experiencing academic challenges.