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This study uses a comparative case study to examine how institutional contexts shape STEM education experiences for students at a Historically Black University and a Predominantly White Institution. Drawing on critical race theory and socio-ecological frameworks, this research investigates how structural, cultural, and andragogy support or hinder STEM persistence for underserved students. Through a review of institutional resources, strategic plans, and missions, three STEM instructors, some of whom now lead colleges, identify barriers and affordances unique to each setting. Findings reveal that while both institutions emphasize STEM retention and equity, they diverge significantly in their strategies—particularly in mentoring and curriculum design. This work contributes to the discourse on race, equity, and institutional responsibility and offers recommendations for leaders.