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How do parents respond to institutional stratification in postsecondary education? Decades of American research show that upper-middle class parents engage in ‘concerted cultivation’(CC) to maximize their children’s chances of entering elite postsecondary institutions. This paper imports this assumption to a strategic testing ground: Toronto, Canada. Drawing on 41 interviews with upper-middle class parents, we find structural differences – specifically the relatively ‘flatter’ institutional hierarchy of postsecondary institutions – has a profound effect on parenting culture. Our data show while Canadian parents engage in CC, they do not associate such practices with postsecondary admissions or stratification. Instead, they rationalize concerted cultivation with broader conceptions of enrichment and self-actualization. We theorize such behavior through an ecological framework which emphasizes the influence of national contexts.