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This paper examines how structural and systemic barriers impede access to opportunities for college and college readiness (CCR) for students enrolled in adult ESL programs and how one community college district has attempted to counter those barriers by adopting an asset-oriented approach that values the rich linguistic, professional, and cultural knowledge of multilingual learners (MLs). Analyzing interviews with students, faculty, staff, and administrators in one urban community college district in the midwestern United States, we discuss systemic challenges facing MLs and highlight three initiatives that aim to bolster their success. We conclude by discussing remaining challenges and offering implications for researchers and practitioners interested in expanding opportunities for college and career readiness (CCR) for MLs and challenging institutional status quo.