Living with a chronic condition (CC) in adolescence has been historically considered protective for risk behaviours. However, research from the last decade suggest that when compared with healthy peers, adolescents living with a chronic condition can engage in risky behaviours in a similar if not higher rate than their counterparts living with out a CC. This study aims to characterize and evaluate the impact of 1) living with a chronic condition (CC), and 2) how the perception of living with a CC affects school participation, and its association with risk/protective behaviours (drunkenness, physical fight, sadness and self-harm). For this purpose 4 groups were identified: adolescents with mostly healthy behaviours, adolescents with mostly risk behaviours, adolescents with mostly risk-internalizing behaviours and adolescents with mostly risk-externalizing behaviours. A large sample was included in this study, composed by 3494 Portuguese adolescents with an average age of 15 years, who participated in the Portuguese Survey of Health Behaviour in School-aged Children/WHO (HBSC). Main results show that adolescents living with a CC have more risk-internalizing behaviours when compared to adolescents without CC, who present more healthy behaviors. Furthermore, adolescents that report that having a CC affects school participation show more risky behaviours than those not affected by a CC who present more healthy behaviours. Boys with a CC show more healthy behaviours, and those who feel that the CC affects school participation present more risky behaviours. On the other hand, girls with a CC have more risk-internalizing behaviours and less healthy behaviours It is important to point out that adolescents living with a CC represent a vulnerable group, and may engage in experimental/risky behaviours as likely as their non CC peers. Thus, potential benefits can arise from reinforcing interventions within protective contexts (family/peers/school setting). Health/education professionals, more than considering risk behaviours as dangerous in themselves, should offer adolescents with a CC an opportunity to reflect on their own decisions. Educational programs would benefit from looking at risk behaviors more from an experimentation perspective, focusing on constructive ways to help adolescents with CC to proceed into adulthood in a more appropriate developmental way.