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Existing research documents class-based disparities in university student experience, and scholars attribute them to differences in the cultural knowledge students’ parents transmit. What remains unclear is how parental immigration status and place of education shape this transmission process. Drawing on 70 in-depth interviews with university students, I find that where parents obtained their post-secondary degrees matters. Parents with North American post-secondary education—whether native-born or immigrant—typically transmit cultural knowledge that is more in-depth, including actionable cultural know-how. By contrast, parents without North American post-secondary education—whether university-educated immigrants with degrees from their sending countries or non-university-educated—typically do not. I argue that student-initiated requests—or their absence—may explain these patterns and play a key role in how in-depth coaching occurs. In families where parents lack North American post-secondary education, students tend to self-select out of asking their parents for advice on university-related matters, as they perceive their parents as lacking knowledge of the post-secondary system. In contrast, in families where parents have North American post-secondary education, student-initiated requests may allow students to retain a sense of autonomy while receiving in-depth parental guidance. These findings advance scholarship on culture and educational inequality by showing how parental place of education shapes the interactional dynamics of cultural capital transmission.