In the US, Latina/os have the lowest levels of educational attainment. Latina/os are increasingly represented in "new immigrant destinations," where educational institutions are poorly equipped to handle the unique challenges immigrants bring with them. My dissertation in a new Latino immigrant community—Elkhart County, Indiana—asks: 1) How do Latina/o young adults navigate the transition out of high school in a new immigrant destination? 2) How does variation in access to school resources, relationships with institutional agents and placements within educational curricular regimes across the local educational context explain variation in pathways formed after high school completion? 3) How do K-12 educational experiences and the transition thereafter shape ethnoracial and undocumented identity formation processes? I find immigrants interfaced with educational contexts that had never considered the needs of this new Latina/o demographic presence. Using qualitative methods, I conducted 67 in-depth life narrative interviews with Latina/o young adults between the ages of 18-26. Over half of respondents were at a critical transition where they are "learning to be illegal" (Gonzales, 2011) beyond the K-12 educational system. The remaining forty percent were 2nd generation: the first cohort of Latina/os who were shaped by the K-12 educational system and are currently "coming of age" in the distinctive context of a new immigrant destination. Analyzing the educational experiences of this overlooked group presents an opportunity to understand the long-term implications for variation in pathways toward mobility.