This chapter traces Indonesia's dominant cultural imaginaries using a sociohistorical approach as an analytical tool. To highlight how these cultural imaginaries operate, it investigates on two cases of task-based learning (TBL) and reflective practice (RP), by examining the structures of local cultures in two geographical sites in Indonesia. The chapter aims to critically reflect that there are cultural constraints when Western educational practices are adopted into local institutions. It presents some cultural imaginaries that can become the site of investigation for further study, through which the process of decolonizing cultural imaginaries can be examined and understood. The chapter also illustrates the nation's conflicting sentiments towards the West, which is simultaneously perceived as both a source of desire and a source of resentment. Finally, it sheds light into how inside forces including Soeharto's neocolonialism, and outside forces such as globalization, are negotiated and appropriated or resisted in Indonesia's educational settings.