Background/Context A large number of emergent bilinguals, also known as English language learners (ELLs), in secondary schools have experienced academic difficulties, grade repetition, inappropriate referrals to special education, and dropout. They are the most in danger of academic failure and in need of highly qualified instruction that meets their needs; however, they have received little attention from schools. To better understand secondary emergent bilinguals’ academic challenges, it would be necessary to examine their learning experiences throughout schooling, including language support programs and services provided, instructional practices and academic support implemented, and assessments administered to make their educational decisions. In particular, as the high-stakes accountability system has played a critical role during their course of schooling, it would be essential to examine how the accountability system has interacted with these underachieving emergent bilinguals. Purpose/Focus of Study This manuscript draws from a larger qualitative study (Kim, 2013) that investigated long-term ELLs’ history of schooling and their perceptions of language and academic learning experiences. The purpose of this analysis is to more closely examine the nature of language support received during participants’ K-12 schooling and their program placements in the context of their performance on state-mandated language and academic achievement tests. Experiences of participants who were retained and referred to and/or placed in special education serve to illustrate schools’ responses to these underachieving emergent bilinguals. Setting/participant This research study took place at a high school in central Texas. Eleven secondary emergent bilinguals who met the purpose of this research project participated in the study. The essential attributes of participants for inclusion were English language learners who (a) met the state eligibility criteria for classification as limited English proficiency, (b) had attended public schools in the United States for seven years or more, and (c) had at least a year of high school experience. Research Design A qualitative research design based on a constructivist, Naturalistic Inquiry (NI) paradigm was utilized to understand the reality of participants’ school challenges. This NI approach is appropriate to analyze concepts and themes derived from the exploratory cases of this population. Data Collection and Analysis Data sources were individual, semi-structured, and in-depth interviews and a variety of school documents that included each student's cumulative folder, Language Proficiency Assessment Committee (LPAC) documents, and academic assessment records. As the constant comparative method of data analysis was a core function of this research process, data analysis occurred concurrently with data collection. Triangulation among students’ recollections of their program placements, archival data, and informant (i.e., district bilingual and ESL professionals) interviews was used to ensure that the findings accurately reflected the actual phenomenon. Member checks, reflexive journaling, and peer debriefing were also utilized to ensure the trustworthiness of the study. Findings Participants in this study experienced multiple layers of limited opportunity to learn as they moved through the educational process. They began their schooling with inadequate bilingual education services in elementary grades, and many of them were retained and/or referred to special education, mainly due to their unsatisfactory scores on state-mandated assessments. Subsequently, participating ELLs all moved up to middle school where they received little English language support; their continued low scores on high-stakes assessments led to placement in remedial programs or intervention courses for state mandated tests. During their high school years, this pattern continued with the addition of End-Of-Course designated courses, remedial courses for preparing for state mandated tests, and credit recovery programs. Though state assessments should not be exclusively used to measure student learning, they were solely used to participating ELLs’ high-stakes instructional and placement decisions (e.g., retention, placement in remedial programs), which appeared to negatively affect participants’ educational trajectory by increasing the gaps in their opportunities to learn. Conclusions/Recommendations The participating ELLs’ experience of schooling fostered academic gaps due to their limited opportunities to learn, and they had been inadvertently excluded from the formal curriculum because schools in the district did not have adequate programs and services to address these learners’ linguistic and academic needs. Informed by social capital framework research and theory, findings suggest that participants’ gaps in learning continued to grow with each subsequent year of schooling, exacerbated by their limited access to appropriate language services and educational support, thereby rendering them struggling, low-achieving, long-term ELLs. Despite their academic challenges, participating ELLs remained eager to succeed in school, which raises a critical question regarding how well the educational system is prepared to provide these emergent bilinguals with high quality, rigorous programs that are responsive to their linguistic and academic needs.