The coping strategies of middle adolescents (14-16 years) generate interest amongst educators, parents, school psychologists and school counsellors. This study, using a phenomenological approach, examined the coping strategies of "problem" adolescents in the Caribbean in regard to their interactions with peers and teachers. Data were collected from semi-structured interviews with a purposive sample of twenty middle adolescents in Barbados. The adolescents' efforts to manage problems in the school environment suggested that they actively sought to prevent problems from progressing to a maladaptive level. An apparent sequence of coping behaviours emerged from the qualitative data analysis. The sequence involves a dynamic process of seven cognitive decision-making and behavioural steps that the adolescents engaged in, in their quest to manage and effectively cope with daily problems. Based on the findings, recommendations are presented for working with adolescents who demonstrate problem behaviours within the school environment.