Cultural analysis of differential minority achievement can create stereotypes and restrict expectations of child performance if group-level cultural generalizations are misapplied to individuals. Observational and interview studies of sibling caretaking and peer assistance in Native Hawaiian contexts illustrate the appropriate comparative analysis of natal and school activity settings. Results indicate Native Hawaiian sibling caretaking varies widely across households and individual child experience. Parents' beliefs about sibcare show a mix of shared acceptance and ambivalence. In natal settings, child-generated activities, carried on without adult intervention, produce most literacy-related behaviors (such as school-like tasks and increased language use). Among the classroom learning activities that are successful with Native Hawaiian children are child-generated interactions, in which children are able to use scripts similar to those observed in natal settings. Other features of natal activity settings (such as personnel, goals and motives, and everyday tasks) are discontinuous with those of the classroom centers. To reduce home/school discontinuities, these data suggest that classrooms need to be accommodated to selected features of natal culture activity settings, rather than be isomorphic in all aspects. Identification of which cultural features these are depends on “unpackaging” cultural effects on individuals by analysis of both natal and school activity settings.