After Hurricane María, approximately 3,500 students enrolled in on Florida's school district from Puerto Rico. Displaced Puerto Rican high schoolers incurred the transitional costs of forced migration at a time in their educational trajectories when they are formulating their postsecondary plans. While student mobility is not uncommon, prevailing college choice models do not account for changes in context. This embedded case study leverages 87 interviews across district stakeholders, including 10 high schoolers to examine whether and how changes in educational contexts (state policy, postsecondary landscape, and schools) influenced changes in postsecondary expectations through the lens of expectancy-value theory. First, Florida's policy context (as an English-only state with English-only testing) created a challenging environment for students to acquire diplomas, which reduced students' "expectations for success." Second, the enrollment patterns and institutional costs were vastly different between Puerto Rico and Florida; Florida counselors were unprepared to help students consider postsecondary options in Puerto Rico and emphasized "utility" and low "cost" of community college. Third, class mattered, as students from higher socio-economic backgrounds were less likely to change their educational expectations, relative to the downward shifts in expectations of low-SES students. We close with implications for college guidance, policy, and research.