This chapter explores the discontinuities in language and literacy practices, from a cultural lens, between home and school for the indigenous Semai community in Malaysia. The focus is to understand how the underprivileged Semai children experience school. Based on a longitudinal ethnographic study with the Semai community, and reflecting on the author’s own home-school literacy experiences, this chapter discusses literacy practices of the Semai children at home and at school. The individual Semai students’ schooling accounts presented in this chapter provide insights that invite the readers to question why—despite the complexity and challenges encountered in the home–school relationship—some underprivileged minority children succeed while others fail.