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Despite increasing attention to college access and transition, little to no research has explored the role of the high school principal in preparing students for college. Drawing on case study methodology and college transition and school leadership theories, we examine how principals endeavor to prepare historically underrepresented students for college success at six early college high schools in an U.S.-Mexico border region of Texas. Our data suggest the importance of institutional partnerships, academic mediation, and student enrichment. Implications for policy and practice are discussed.