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The transition to life after high school is a consequential juncture that holds long-run implications for students’ economic, educational, and social well-being. Students confront choices about postsecondary study and work, shaped by their goals, skills, constraints, and the context that surrounds them at the time they must make such decisions. Young adults are especially sensitive to economic downturns (Hoynes et al., 2012), and typically enroll in college at higher rates during periods of weak labor markets and rising unemployment (Barr & Turner, 2013; Schanzenbach & Turner, 2022). However, the COVID-19 pandemic affected the delivery of higher education, abruptly shifting coursework online, alongside its negative shocks to health and social aspects of daily life. In this paper, we examine changes in postsecondary and employment outcomes for cohorts of high school graduates who straddle the COVID-19 pandemic. We use administrative data from a large, socio-demographically diverse school district in the United States, and focus on an outcome, opportunity youth status, that captures disconnection from postsecondary study and work. We find that graduating during the pandemic increases the likelihood of opportunity youth status during the six months following high school graduation by between 2 and 4 percentage points, compared to observationally similar high school graduates in pre-pandemic cohorts. This change in opportunity youth likelihood represents a considerable increase—of between 23% and 46%—over the pooled pre-pandemic mean rate of 8.7%. The pandemic-related jump in the likelihood of opportunity youth status is largest among Hispanic students. For graduates in the classes of 2021–2023, the heightened disconnection from college and work persists for up to two years following high school graduation, pointing to more than transient disruptions to avenues for young adults to acquire human capital, build skills, and secure employment. Shifts in students’ intentions about life after school alongside lower likelihoods of realizing those aspirations as the pandemic unfolded both contribute to these findings.