This article is about the tragic journeys and livelihood insecurities of coastal fisherfolk of India and Sri Lanka, who are arrested and jailed by these countries for having entered each other’s arenas. These fisherfolk are victims of defined and undefined boundaries in the seas, and increasing conflicts over renewable resources. The article questions the cartographic and border anxieties of these countries, which come into fundamental contradiction with the lives, livelihoods and desires of the majority of coastal fisherfolk, who are short-term migratory subjects on an everyday basis. They are constantly subjected to categories such as insider and outsider, safety and danger, domestic and foreign, self and other. At the same time, the article reveals how these fishing communities themselves mark an ambiguous space, located as they are on the margins of the two countries, thereby providing emancipatory possibilities that can emerge from the spatial freedoms which they have practised. However, there are also some contradictory voices. Some of these fisherfolk are articulating the very same language which is used to suppress them. In attempting to highlight these complexities, the article widens our definitions of migrations, diasporas, and transnational subjects.