Based on nine months of ethnographic fieldwork, this article explores the contested roles of education in the intergenerational dynamics and transcultural negotiations of immigrant Chinese in Luxembourg. It offers an account of how immigrant youth and parents exhibited particular cultural orientations and social ties that helped them gain collective wellbeing yet also produced intergenerational and cross-cultural tensions in childrearing and schooling. Immigrant-specific social and cultural resources -- as reflected in children's labor participation in family catering businesses and parental high academic expectations -- are both a source of empowerment for immigrant survival, and a source of constraint when leading to racial stereotyping and tensions in home-school, parent-child relations. This paper calls for culturally responsive schooling in order to better understand immigrants' multi-pronged challenges, resources, and aspirations in negotiating educational inequalities. This study hopes to contribute to scholarship on immigrant education and European Chinese diaspora more broadly.