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First-generation students experience a number of postsecondary complexities compared with their continuing-generation peers, including challenges associated with academic and financial support for college, cultural, social, and academic transition, and college retention and persistence. There is a clear need for increased focus on and examination of educational features, opportunities, and competencies that promote first-generation students’ academic achievement. Leveraging data from the Study of Deeper Learning, this poster summarizes major findings from an analysis of the postsecondary pathways of first-generation students and the self-regulatory competencies that promote their postsecondary success. Standardized measures of content standards achievement were obtained in grade 8. Measures of motivation to learn and self-efficacy were obtained in grades 11 or 12 using a cohort design. Coarsened exact matching was implemented to closely match students who attended and did not attend deeper learning schools based on key background and demographic characteristics, including first-generation status. Core content knowledge and application of higher-order thinking skills were assessed in reading, mathematics, and science. Postsecondary outcomes included postsecondary persistence and attainment of a four-year college degree. Structural regression modeling tested direct, indirect, and conditional effects of deeper learning and first-generation status on students’ knowledge and postsecondary outcomes. Findings revealed unique and differentiated effects on content knowledge, persistence, and degree attainment. Deeper learning attendance predicted content knowledge and persistence, both directly and indirectly via self-efficacy. Attending deeper learning schools exerted conditional and facilitative effects on content knowledge and persistence specifically for first-generation students. Implications for policy and future research are considered.