What happens when moments of crisis, in the form of unprecedented global events, withdrawal of state legitimacy, or stigmatization and attacks by the local community, challenge the “stable world” of migration agents and potentially disrupt order in the brokerage industry? This chapter draws attention to such events, analyses the contestation of order posed by moments of crisis and examines the responses of migration agents towards them. Drawing on ethnographic data and analysis of social media posts and public engagements of migration agents and tapping into the analytical framework of market legitimization, this chapter enables us to see how the brokerage market, once formed, cannot sustain itself on its own but requires constant negotiations and adaptations with the state and society. The findings of this study further contribute to our understanding of emerging trends and practices within migration brokerage in Nepal, such as altruism among the agents or the use of ‘ethical recruitment’, that seek to re-legitimize the market and the social identity of the agents. This illustrates that legitimization of markets is an ongoing and ever evolving process, and brokerage a contingent and contested practice.