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Children’s future orientation—their expectations and aspirations—has a consistent and substantial effect on a variety of life course outcomes. However, little research to date has considered empirically how future orientation is shaped by adverse events such as experiencing a parent be incarcerated. I leverage the unique nature of Add Health’s retrospective parent incarceration questions to employ an innovative analytic strategy that accounts for selection bias and unobserved heterogeneity above and beyond typical observational methods in this area. Results indicate that paternal incarceration reduces youth future orientation by nearly a full standard deviation and are robust to a variety of models and specifications. Given that parental incarceration is increasingly common and disproportionately experienced by disadvantaged youth, the large magnitude and causal nature of my results reveal an important pathway through which mass incarceration has contributed to the intergenerational transmission of inequality in the U.S. in recent decades.