The first Macanese diaspora to Hong Kong in the 1840s saw not only the movement of Macau’s Luso-Asians to British territory, but also the unfolding of decades of discussion regarding the repressive rule of the Portuguese colonial administration over Macau. From establishing Portuguese-language newspapers to writing to Hong Kong’s English-language newspapers, the Macanese found a relatively liberal space in British Hong Kong to address Macau’s social and political issues and criticise the Portuguese colonial administration and Portugal away from the Portuguese empire’s strict press censorship. Through exploring the ways Macanese newspaper editors and contributors challenged Portuguese policies and maladministration on British soil, this study aims to first, analyse the experience of Hong Kong within the wider context of British press control in its Asian colonies and second, show how trans-border interaction came to be facilitated between Hong Kong and Macau by the movement and activities of a multiracial diasporic community.