There has been a long history of intermediaries shaping low wage or unskilled mobilities between South India and Singapore. Starting with the movement of indentured labour in the colonial period and the kangani system to more networked forms of migration in the contemporary era. Today, those same transnational trajectories continue, primarily with low waged migrants from the Indian state of Tamil Nadu. These men and women are considered temporary migrants who do not have access to any pathway to citizenship or permanent residency beyond the tenure of their work contracts. Much of this migration takes place through intermediaries in both India and Singapore, who often demand very high recruitment fees in order to secure a job for the potential migrant. Already in a precarious position due to their immigration status, they are further indentured through their debt bondage as a result of the high costs of mediated migration. Drawing from interviews with return migrants and migration agents in Tamil Nadu, this chapter understands the role of trust, kinship, and village networks, and the lure of transnational migration to Singapore as interlinked with the continued exploitation of low wage migrants. While labour recruiters play the dual role of enabler and exploiter, this chapter also points out that it is also employers and a system that displaces authority from both sending and receiving states that are responsible for structural disadvantages that low waged migrants from India to Singapore continue to face.