This study presents a sociological analysis of childrearing practice in terms of career and behavior supervision over children. Taking social class into account, it reexamines a prevalent assumption concerning educational inequality: the stronger the cultural continuity between family and school, the better will be children’s future opportunities. For empirical purpose, qualitative methods such as participant observation, semi-structured interview, and document analysis were used to collect data from two primary schools in northern Taiwan. The major findings are as follows. (1) So far as career supervision is concerned, supper-middle class parents get more thoroughly involved in their children’s educational and occupational preparation, while their working class counterparts take somewhat more passive and fatalistic attitudes. (2) As for behavior supervision, upper-middle class parents appear more democratic and working class parents by comparison more authoritarian. (3) No matter in respects of career supervision or behavior supervision, teachers adopt almost the same way as parents do to supervise students from each class, thus setting up a corresponding link between schooling and parenting in a class-specific way.