This chapter centres on Macau’s experience from the occupation of Hong Kong in December 1941 until the end of the war in September 1945, when the enclave became the last foreign-ruled territory in China to remain unoccupied by Japan. It argues that collaboration through compliance was a way of avoiding occupation. In this period, the practice of neutrality in Macau reached a peak of ambiguity. It was marked by the interplay of different forces and important new players competing for political legitimacy, economic control and social influence. These included Chiang Kai-shek’s government, Wang Jingwei’s Reorganised National Government, Portuguese colonial authorities, Japanese military forces and local elites.