The present study explores the concurrent contribution to sleep problems of individual-related, family-related, and school-related factors in adolescence. Gathering from the Italian 2018 Health Behavior in School-Aged Children (HBSC) data collection, we used hierarchical logistic regression on a sample of 3397 adolescents (51% females, Mage = 13.99, SD = 1.62) to explore the contribution to sleep problems of the individual (Model 1: alcohol use, smoking, screen time, physical activity), familial (Model 2: parental communication, parental support), and school-related (Model 3: peer support, schoolmates/students support, teacher support and school pressure) variables. 28.3 percent of adolescents reported having sleep difficulties. Overall, Model 3 significantly improved over Model 2 and Model 1. Data showed that increasing smoking (OR = 1.11; 95% CI: 1.03–1.20) and screen time (OR = 1.05; 95% CI: 1.02–1.08) were associated with sleep difficulties but not alcohol use and physical activity. Also, impaired communication with both parents and increasing parental support (OR = 0.84; 95% CI: 0.78–0.90) were associated with decreased odds of sleep problems. Finally, both increases in school pressure (OR = 1.40; 95% CI: 1.26–1.56) and lack of student support (OR = 1.25; 95% CI: 1.10–1.42) were associated with a higher likelihood of sleep problems, while peer support and teacher support were not.Conclusion: Our findings highlight the importance of an integrated approach to the study of sleep difficulties in adolescence that includes specific psychosocial contributors such as the quality of parental communication and perceived parental support and considers the quality of the day-to-day relationship with schoolmates and the school level of demands.What is Known:• Adolescents' are at-risk of more significant sleep difficulties, and recent literature highlights the importance of an integrated approach to understanding this phenomenon, including biological, psychosocial, and contextual factors.•The literature lacks findings that consider the concurrent contribution of individual and psychosocial factors to sleep difficulties in adolescence.What is New:•The quality of parental communication and perceived parental support, as expressions of adult figures' emotional and behavioural availability in the adolescent's life, are significant determinants of sleep difficulties.•The quality of day-to-day relationships with schoolmates and the school level of demands contribute to adolescent sleep problems.