In this study, we explore academic procrastination and associated motivation variables in 612 adolescents from Canada and Singapore. Few studies have explored adolescent procrastination and no previous studies have investigated adolescent procrastination using a cross-cultural framework. Singaporean adolescents reported higher levels of procrastination and lower levels of self-efficacy for self-regulation than Canadian adolescents. Males across settings reported higher levels of procrastination and lower levels of self-efficacy for self-regulation than females. Bivariate relationships between procrastination and the motivation variables showed similar patterns in Singapore and Canada. Multigroup structural equation modeling revealed that self-efficacy for self-regulation showed the strongest multivariate relationship with procrastination for adolescents in both settings. The article concludes with implications for practitioners and researchers.