Immigrant students access community colleges with increasing frequency (Teranishi, Suarez-Orozco, & Suarez-Orozco, 2011); however, the majority of research focuses on Generation 1.5 students who completed K-12 education in the U.S. Generation 1 learners are defined in this study as adult immigrants (Rumbaut, 2004) and adult learners (Knowles, 1970) who began American education in adult ESL. Learners' unique experiences and social roles motivate their transition to higher education and produce distinct linguistic and cultural needs. Many immigrant students begin in developmental education (Teranishi, Suarez-Orozco, & Suarez-Orozco), which is strongly influenced by the adult learning theory of andragogy (Knowles, 1968). This multiple case study explored how Generation 1 learners experience transition into developmental education, conceptualized as placement testing, advising, tutoring and integrated reading and writing class at one community college. Findings indicate that learners exit adult ESL when they feel it no longer meets their academic and personal needs. Transition is a complex process by which learners' identities become sites of contestation as they negotiate membership into imagined communities of various college spaces. Misalignment between learners' understandings of what it meant to be a college student and college expectations, which were rarely explicit, resulted in others' delegitimization of learners' participation or rejection of the learners' chosen identities. Learners' participation rights were dependent upon their abilities to apply symbolic capital to gain acceptance of their specific identities. The study highlights essential differences between Generation 1.5 students and Generation 1 learners based on learners' multiple social roles and previous experiences; the work problematizes andragogy (Knowles, 1968) suggesting that educational contexts powerfully shape Generation 1 learners' transitions. The work concludes with practical applications for supporting Generation 1 learners in developmental education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]