This chapter employs concepts of liminality, uncertainty, and precarity to analyze mismatches between the lives of immigrants and the forms of deservingness acknowledged in US immigration policy. In the current atmosphere of heightened enforcement, “deservingness” has been defined in a constrained fashion that privileges sacrifice, achievement, personal responsibility, and law abidingness and that ignores the structural conditions that shape immigrants’ lives. Educational pursuits are particularly fraught, as schooling is a protected space and life stage, yet is also shaped by economic disadvantage, immigration enforcement, and racial and ethnic disparities. The chapter draws on two sets of data: (1) interviews conducted between 2006 and 2010 with fifty young adults who immigrated to the United States as children and (2) interviews carried out between 2014 and 2017 with Latinx and Asian and Pacific Islander immigrants who either had DACA or who had hoped to apply for deferred action through programs that were never implemented. This material demonstrates the ways that structural conditions impact educational opportunities as well as the resourceful strategies through which interviewees, their families, and some educators pushed back against these forces to nonetheless pursue educational goals.