This chapter supplies a diachronic analysis of language policies and practices in Sri Lanka in the pre-colonial, colonial, and immediate postcolonial periods, based on the model we introduced in the previous chapter and elaborate in the next. We focus on key decisions and status planning in relation to languages, discuss the motives and intentions of various stages, and how they intersect with local or endogenous sociolinguistic and political milieus, and external developments. Regarding the latter, the focus is on English, which ‘returns’ to Sri Lanka as a commercial and global language after being banished, as it were, as Ceylon’s colonial language. The transition between an immediate post-independence Ceylon reconstructing its national identity and presence in its region and the wider world, in line with many post-colonial Asian and African societies, and a later Sri Lanka, transformed into an executive presidency, having undergone the trauma and upheaval of civil war and communal conflict, is both radically different yet eerily similar. The similarity consists in how key questions of pre-independence thought would be addressed, especially regarding the need to accommodate all the component communities, their languages, faiths, and cultural characteristics, within a united and cohesive society. The education system has been the site of diverse experiments in plural education, yet despite political turmoil and education experimentation, critical problems remain. Our focus is primarily on language in education, but this needs to be set against the status of languages within institutions and economy of the wider society and its legal frameworks.