For close on half a century, the British naval dockyard in Singapore was a prominent employer in the colony. The huge facility attracted migrant workers from the region, and entire settlements and communities were established around the premises of the dockyard as well. This article seeks to place the legacy of Singapore's naval-base workers within the historical contexts of the entanglements between imperialism, diaspora, social movements, and labour resistance. The development of international labour flows, formation, and identity was reflected in the prominence of the migrant Malayalee community and its socio-religious organizations at the naval base. Furthermore, the routine individual defiance and industrial unrest went beyond disputes about wage levels and working conditions. They were enmeshed within the broader undercurrents of Singapore's transitory political culture, and between the interwar decades and the period of decolonization disturbances at the naval dockyard became part of larger political contestations.