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Long-term, adolescent English language learners experience persistent academic underachievement in spite of several years of schooling; yet the research on this topic is scant. To increase our understanding of these students’ educational and linguistic experiences, we examined perceptions of 13 long-term ELLs about their schooling in the context of their school history, including program placements, special education referral, and academic outcomes. Data from semi-structured interviews and documents were analyzed using a grounded theory approach. Participants viewed themselves as English-proficient, motivated learners, and described their school experience as positive but challenging. The findings revealed a gap between their postsecondary aspirations and the reality of their academic performance, which have implications for research and practice.