Based on 30 semi-structured interviews, I analyse the stories high-skilled immigrants told about their legal trajectories since their arrival in the United States. I explain immigrants’ two pathways from temporary or risky legality to permanent or secure legality: the Uninterrupted Pathway to Legalization and the Contingent Pathway to Legalization. Specifically, I explain how navigating a temporary, or risky, legality before acquiring permanent residency privatizes risk by forcing immigrants in the second pathway to shape their legal trajectory for themselves. Given that high-skilled immigrants spend many years under temporary legal statuses, in a context of legal uncertainty and an indeterminate timeframe for achieving permanent residency, high-skilled immigrants embrace an involuntary agency. Privatization of risk refers to the shift in the cost burden of the legal path towards permanent residency. The burden has shifted from institutions – the employer and the government – to high-skilled immigrants themselves.