The border between the Japanese nation and its colony initiated human migration from Yaeyama to Taiwan. Okinawan immigrants were people with diverse ages and social backgrounds. Yet there were some shared characteristics across generations and types of immigrants. Whereas it was not uncommon for individual Yaeyama islanders to spontaneously migrate to Taiwan, numerous islanders migrated there with family members. Some of them gave birth in Taiwan. Others brought very young children. The second and third generations of Yaeyama immigrants shaped very different identities from the first generation. Although all three generations were labelled “Okinawans,” the second and third generations understood “home” to be not Yaeyama, but colonial Taiwan. Okinawans had active agency in making, maintaining, and shifting borders and boundaries between the metropole and colony in imperial Japan.