Introduction: High school students' self-reports about their perception of barriers, optimism and attachments in relation to the postsecondary transition were examined. Method: Factor analysis of an inventory administered to 1044 high school students (573 males and 471 females) who attended six urban schools in Scotland identified three factors. Results: ANOVA indicated that students living in areas of higher deprivation reported perception of more career barriers and fewer career scaffolding attachments. Males were more optimistic about their career prospects but reported fewer career scaffolding attachments. There was an interaction between deprivation and gender with regard to career optimism. Discussion and Conclusion: These results contribute to an explanation of why failure to obtain a positive postsecondary destination is more prevalent in young people living in areas of greater social deprivation, and in males rather than females. The implications for practice, policy and future research are discussed.