It seems undeniable that immediate social contexts exert an important influential role on adolescent behavioural adjustment. Research thus far has found that certain family, school and community/neighbourhood environment characteristics may influence a youth's involvement in risk activities such as antisocial behaviour and drug use, and even delinquent behaviour. However, the mechanisms that link these characteristics to such behaviours have not yet been thoroughly analysed and prior research has focused mainly on adult populations. The objective of this study was to analyse the joint contribution of specific factors, deriving from family, school and society, which have an effect on levels of drug consumption, antisocial and offending behaviour, in a sample of 2528 youths (aged 10 to 16). In particular, in accounting for involvement in risk activities and ultimately in offending behaviour, we examined interactions among the following variables: living in a disadvantaged community, quality of relationship with parents, distrust in local police, attitude to social norms, and rejection of and from school (truancy, suspension and expulsion). A structural equation model was calculated to account for these interactions, which revealed patterns of influence with important practical implications related to social policies on risk behaviours in adolescence.