This study examined the differential experience and educational outcomes among two English Language Learning (ELL) student cohorts, namely holders of a high school diploma and individuals who did not complete high school. Our analysis of 39 interviews with ELL respondents demonstrated that premigration experience; personal qualities; interactions at home, in school, and in the community; as well as peer influence, have shaped the differing experience and inequitable educational outcomes of ELL students. The findings brought attention to the areas of support for all ELL students, including quality classroom instruction, explicit and structured ELL education, supplementary academic and literacy programs, responsive psychosocial support, and access to positive mentors.