Long-term, adolescent English language learners (ELLs) 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 experiences, we explored 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 semistructured 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 raises questions about the adequacy of educational programs and identification of ELLs with disabilities.