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This article examines two US migration lotteries, the diversity visa (DV) and the H-1B visa programme, and explores the impact of ‘winning the lottery’ on (im)migrants in the United States. Drawing on 107 semi-structured in-depth interviews, we show how US immigration policies impact several spheres of migration lottery winners’ lives. We push past the binary of legal/undocumented status to show that specific design features of these lottery programmes have deleterious effects on immigrants and compromise the goals of US immigration policy. Though the diversity visa and H-1B visa programme are different in their design and intended impact, an analysis of these two programmes reveals the variation in experience and outcome of immigrants who enter the country legally. We find that winning the diversity visa lottery caused disruptions in the lives of winner migrants, especially in three key areas: preparedness to migrate, education and work, and marriage and family. Our findings show that H-1B visa migrants are vulnerable to exploitation in the labor market, are blocked from fully developing their human capital potential, and feel a sense of transience in the US linked their tenuous of their legal status. Our analysis draws attention to typically overlooked aspects of legal statuses that negatively impact migrants’ experiences and impede immigrant incorporation. The article seeks to add to theorization on the role of US immigration policies and law in shaping (im)migrant incorporation.