This chapter shows how the colonial and post-colonial experiences of a recently independent nation influence contemporary perceptions of multilingualism in language education planning. A mother-tongue pilot project in Timor-Leste provides an illustrative case. The chapter outlines the policy developments that preceded the project and sketches the complex interactions among the disparate actors involved. In taking stock of the project’s setbacks, threats, and challenges and considering its prospects, the chapter suggests that it is the accruing injuries of coloniality that lead many social actors to regard Indigenous languages as unfit or not yet ready for use in the modern curriculum. The story of the pilot project offers insights into the discourses that influence language policy debates and the kinds of historical and contextual conditions that influence perspectives on multilingualism in southern settings.