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Existing studies on middle-class parenting have identified that upper- and middle-class parents are heavily involved in arranging their children's academic and leisure activities. Nevertheless, comparative research focusing on the local ecology in different countries has highlighted how and why these parents raise their children varies across societies. Using interview data collected from 22 Chinese upper- and middle-class parents and their children, I show how affluent parents adopt a style I call assistive parenting to help their children navigate transnational undergraduate education. I find that, being embedded in the local ecology of the Chinese education system, these parents' upbringing, their children's encounters with the public education system, exposure to popular parenting knowledge, and their parenting goals of raising well-rounded children contribute to their emotional unwillingness to push their children hard for status maintenance through public education. Moreover, students’ switch from the Chinese public education system to the international education system caused cognitive struggles since these parents lack knowledge of navigating foreign college applications. Therefore, instead of directly involving themselves in their children's decisions and preparations for studying abroad, these parents closely followed their children's requests to improvise interventions by utilizing and expanding social networks and outsourcing to independent education agencies.