As colonial subjects acquired Britishness, how did such newly acquired identities interact with their existing identities and identifications? This chapter explores the ramifications of colonial subjects acquiring Britishness by drawing from the experience of the Hong Kong-Portuguese (more commonly termed ‘Macanese’ now). Through education and participating in public services, Portuguese Eurasians in Hong Kong took both an active and passive role in acquiring Britishness. While on one hand institutional discrimination made it too obvious to them that state authorities never fully accepted their Britishness, on the other they became too British in the eyes of other Portuguese communities in the region. Using newspapers, family papers, and oral history, this chapter examines this acculturation process, and the tensions and backlash this process engendered for the community.