This phenomenological study includes exploration of the instructional experiences and the schooling factors that have been in place both assisting and failing academically six long-term English learners who attend a comprehensive urban high school in Los Angeles. Long-term English learners have attended schools in the United States (U.S.) for more than six years and are not yet fully proficient in English. Qualitative and quantitative data sources, include demographic questionnaire, one-on-one focused interviews, classroom observations using English learner Shadow Study Protocol (Soto, 2012), academic transcript analysis, and a focus group, were analyzed using descriptive content analysis and Critical Sociocultural Theory (Handsfield, 2012; Lewis, Enciso, & Moje, 2007). The researcher identified two instructional experiences-lessons not engaging students in social interactions or learnercentered activities, and instruction did not help students gain proficiency in the English language-that hindered these students’ advancement-and three schooling factors-enrollment in Structured English Immersion (SEI) programs throughout schooling, lack of knowledge about the reclassification process and low academic literacy skills and lack of understanding of how to succeed. To remedy this situation as it impacts numerous students, Legislators should pass laws that support bilingual education and schools should offer English learners the opportunity to develop their native language to be successful in developing bilingualism.