This research investigated longitudinally the role of debt in a cohort of 1232 final-year New Zealand secondary school students. Two surveys were conducted to address students debt and savings behaviour and estimates, tertiary education entry decisions, and attitudes to tertiary education and term-time working. Debt attitudes were found to be more complex than previously proposed, and this has significant ramifications for debt attitude theory and research. Longitudinal comparisons suggested students become more or less avoidant of debt depending on their circumstances. However, debt attitude results still support many of the findings of earlier research such as debt acquisition preceding a more tolerant attitude change. Debt and tertiary education attitudes are not well predicted. Students report engaging in term-time working to limit their student loans, but engaging in term-time working results in lower grades in their studies. Those from the middle and higher socio-economic classes are more likely to be positive towards tertiary education, and thus entrants, compared with the lower socio-economic classes.