Seeking to offer new interpretations on the life and times of Portuguese political deportees, this article focuses upon the remote Southeast Asian half-island colony of Timor as part of a far-flung network of prisons carried through under the authoritarian regime of António de Oliveira Salazar. First, it looks back at the political and economic instability in Portugal following the military coup of May 1926 ending the First Republic. Drawing upon newly available documentation, the article examines two waves of deportees from Portugal arriving in Timor, youthful activists involved in anarcho-syndicalist activities in the 1912–1927 period, and a more senior leadership group involved in a failed military coup of August 1931. It then tracks the reactions of the deportados to Japan's wartime invasion and occupation of Timor including exile in Australia. By highlighting the role of anarchist revolutionaries in Portugal from the 1920s and their subsequent incarceration in Timor, the article also draws attention to the dynamic linking metropolitan centers with their far-flung colonial peripheries at large. In the case of the Portuguese empire, as argued, the burgeoning anti-colonial movement of the 1960s would also intersect with the pro-democracy movement at home. Inside Timor, moreover, deportado families emerged as part of the pro-independence movement indelibly imprinting politics in the post-colonial era.