Background/Context The label long-term English learner (LTEL) is increasingly used to describe students who have been educated in the United States for many years but have not met criteria to be considered proficient in English. Though created to draw awareness to the unique needs of a particular group of students, the LTEL label has acquired strongly negative connotations, with descriptions of LTELs often focusing on students’ perceived deficits. Limited empirical analysis of achievement and other outcomes among this group of students has been conducted, and little is known about the impact of the LTEL label on students’ educational trajectories. Purpose/Objective This study explores the characteristics and educational trajectories of students considered long-term English learners. In addition, the study explores the costs and benefits associated with the LTEL label. In particular, the author examines how prolonged classification as an English learner impacted students’ opportunity to learn and explores whether and how the LTEL label was linked to stigma for students. Research Design Using case study research methods, this study focuses on the experiences of three students in a medium-sized California school district who were considered long-term English learners. Analysis of district-wide, longitudinal data contextualizes the experiences of the three focal students. Findings/Results First, findings provide evidence of the heterogeneity of academic achievement, course placement, and long-term outcomes among students to whom the long-term English learner label is applied. Approximately half of students considered LTELs in the district had met at least some of the criteria necessary to be considered English proficient in at least one year. For instance, one focal student remained an English learner throughout middle school solely because of her scores on the state standardized math test. Meanwhile, 35% of students in the district who were considered LTELs also qualified for special education services because of documented disabilities. Second, findings indicate that there was a loose coupling between the LTEL label and specific services for students in this district. Among the three focal students, all could be considered LTELs, but their course placements and the academic rigor of their courses varied dramatically in high school. Finally, students experienced courses designed exclusively for English learners at the secondary level (but not at the elementary level) as stigmatizing. Conclusions/Recommendations Given the substantial variation among students to whom the Long-Term English Learner label is applied, this research suggests that educators and policymakers should use the LTEL label with caution. For example, “intervention” courses designed for LTELs at the secondary level may need to be reconsidered, taking into account the unique needs of the particular students the courses are intended to serve. Given the stigma that students associate with EL-only courses at the secondary level, the conditions under which such courses can function as empowering rather than stigmatizing spaces represents an important area for future research.