This chapter approaches the long history of the Portuguese Empire in the Asia-Pacific world through a micro-history of a paradigmatic colonial object: national flags.1 It analyses the ‘fantastic stories’ told by the nineteenth- and twentieth-century Europeans about the Indigenous cultural appropriations of Portuguese flags in East Timor – the eastern half of Timor island, a small but durable Portuguese establishment from the 1500s until 1974 – with a view to discussing the complex exchanges between Indigenous people and European objects from overseas. From the outset of Portuguese imperial expansionism in the 1500s, flags accompanied Portugal’s ambitions and became an ubiquitous presence throughout the Portuguese imperial world for centuries. They were handed over to the rulers of Indigenous polities as tokens of Portuguese kingship power, as vassalage gifts in exchange for allegiance and obedience to the Crown of Portugal. This was initiated by early modern strategies of conquest and vassalage expansionism that in some settings seem to have persisted until the 1910s. It was the case of East Timor. In this remote but lasting Portuguese colony in the Asia-Pacific region, flags of Portuguese origin became significant not only in the practices and imaginaries of Europeans, but also in the Indigenous societies that, at some point in the past, had forged ties with the Portuguese – and in this process came into possession of Portuguese flags.