The paper proposes a critical understanding of contemporary “low-skilled,” transnational contract work/circular migration as a guest-worker regime. Rather than approach circular migration as an instrument of development, or a human rights problem, this paper situates it within the larger, historical debates over the status of labour that emphasise questions of surplus extraction. Drawing on ethnographic research among Bangladeshi male migrants in Singapore and return workers in Bangladesh, the paper explores two crucial moments in the life of migrants—of choosing overseas contract work, and of leaving. In each moment, it highlights certain mechanisms that push migrants along the porous line between free and un-free work, incrementally toward the latter.