The journey to higher education by undocumented students has been one of legal, financial and informational barriers. Despite ensured equal access to primary and secondary education, federal policies addressing access to post-secondary education are non-existent – a lack of action that has motivated some states to provide additional access and others to erect further barriers. While the implementation of the Deferred Action for Childhood Arrivals (DACA) programme in 2012 has attenuated the transition to ‘illegality’ that many undocumented young people experienced after high school graduation, access to post-secondary education remains a challenging endeavour for most undocumented youth. The recent announcement to rescind DACA and the lack of a solution for comprehensively managing immigration further obscure the future of this constituency. Placed at the intersection of contrasting political, economic and social contexts, this chapter explores the experiences of three undocumented immigrant youth in Texas who enter adult transitions at differing levels of educational attainment. This chapter illustrates how policies, school practices and families’ legal structures continue to create conflicting educational experiences of exclusion and belonging for undocumented young people living in the United States.