This study analyzes Deeper Learning (DL) opportunities and the correlation between multiple DL measures on STEM (science, technology, engineering, and math) career orientation in out-of-school time (OST) STEM programming. Additionally, this study examines the presence and validity of the American Institutes for Research (AIR) DL measures in OST STEM enrichment program evaluation, and DL's ability to help address equity issues in STEM education for diverse learners. For analysis, this study examined longitudinal data (pre- and post-surveys) using confirmatory factor analysis (CFA) and design-based multilevel structural equation modeling (MSEM) from a large-scale OST STEM enrichment program with multiple sites across the state of Texas (22) that serves middle and high school students who participated for seven weeks over the summer in 2019 (n = 1,447). Results showed that the AIR-DL measures were suitable for use in OST STEM enrichment programming and that DL opportunities measured through critical thinking, communication and collaboration, and real-world connections had positive effects on STEM career orientation, especially for women and underrepresented minority students. Implications for theory, practice, and future research are briefly discussed.