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This study asks how upper-middle-class (UMC) parents in Canada and Germany leverage cultural and economic resources to transmit advantages to their children, contrasting their strategies with those prevalent in the U.S. Utilizing a Bourdieusian framework, we explore whether parents adopt the intensive “concerted cultivation” model or embrace a more relaxed approach in less stratified educational contexts. Through qualitative interviews with 165 families, we analyze parenting logics, educational investments, and financial planning. Our findings reveal significant national differences: Canadian and German parents prioritize children’s interests and happiness over status competition, focusing on financial security and resilience rather than upward mobility. This research enriches the understanding of social reproduction and the role of intergenerational wealth transmission across different national contexts.