With an international focus, this chapter analyses Portuguese neutrality in wartime China before the fall of Hong Kong in late 1941, with reference to the British and Japanese imperial presence in the region. It argues that the war in South China saw Macau and its Portuguese administration engaged constantly with these two major imperial powers in a precarious balance marked by continuities in Portugal’s relations with its old ally, the United Kingdom, and a novel proximity to Japan that generated contradictory practices on the ground.