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First-generation college students (FGCS) bring meaningful strengths to their educational journeys, yet the high school supports that most influence their postsecondary transitions are not well understood. Using a Funds of Knowledge framework, this study examines how Deeper Learning opportunities, including real-world connections, personalized support, belonging, and postsecondary guidance, shape enrollment outcomes for 921 FGCS. Data from the Study of Deeper Learning were merged with National Student Clearinghouse records and analyzed using multi-group structural equation modeling. Early findings show similar levels of real-world connections across school types, while students in network schools report higher belonging and postsecondary support. These patterns highlight the potential influence of school climate and relational supports on FGCS college enrollment.