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At a time when youth of color, particularly those from low-socioeconomic status communities, continue to experience limited access to higher education, this paper points to possibilities for identifying and leveraging moments of possibility supportive of youth’s college readiness and access. This paper presents findings of an 18-month qualitative study situated in the context of a literacy-and-songwriting program run by a community-based organization in Detroit. Findings consider whether, how, and why moments of possibility may be strategically utilized as a means to support youth in navigating barriers to their college access. Recommendations are provided for educators and community-based partners seeking to create more equitable schooling experiences, college readiness, and college access for youth of color.