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This qualitative study explores how rural students navigate their transition to a large, flagship Midwestern university. Guided by Rural Transition Theory (Kearney, 2019), we analyzed interviews with ten rural undergraduates, highlighting the structural, cultural, and developmental challenges they faced as well as the assets and strategies they used to succeed. Findings affirm and extend RTT and the three theories upon which it is based, revealing nuanced experiences related to social capital, academic preparedness, and identity dissonance, while also underscoring students’ agency and resilience. This work contributes to research and practice by informing more inclusive and identity-affirming supports for rural college students and advancing theory on rurality as a key factor in postsecondary transition.