Using Bronfenbrenner\'s theory of development, the study explores how SES variables, parenting and school perceptions relate to motivation, coping, optimism and academic achievement for students at-risk of dropping out of school. Typical, resilient and students at risk were compared (n=1127) using qualitative and quantitative methods. Findings show students at-risk experience significantly higher levels of neglectful parenting, lower school perceptions (teacher relationships, curriculum satisfaction and positive school affect) higher suspension levels, and blended or single-parent families where parental education is limited to high school and at least one parent is unemployed. By contrast, resilient students, whose socio-demographic characteristics places them at-risk of dropping out, report parenting characterised by high levels of supervision. Like typical students they have high self-efficacy, mastery and positive coping and low self-handicapping and projective coping. Bronfenbrenner\'s theory was validated as school views were positively correlated to parenting in typical students, but not in resilient or students at-risk.Findings of the study will be of interest to educators, guidance officers, parents and academics.