This article rethinks a Luso-Asian community that existing literature has termed ‘Portuguese’ or ‘Macanese’ by exploring the differences between the Macanese communities of Macau, Hong Kong and Shanghai. It examines inter-port debates between 1926 and 1929 that triggered wide discussion in Portuguese and English-language newspapers regarding the political loyalty of the Macanese. Set against the framework of a burgeoning print capitalism and vibrant associational culture in Asia’s port-cities, the article argues that varying urban circumstances and political structures influenced the negotiation of the Macanese between imperial, civic and colonial identities to eventually construct three new imagined communities.