Preparing high school students to skillfully and successfully navigate the pathway to college is a growing concern among researchers and policymakers. This issue has raised important questions about what urban school districts can do to build capacity among their high schools to guide students and families toward successful college transitions. This analysis examines how district-level policies impacted the capacity of two urban high schools to establish and maintain college counseling strategies that effectively prepare students to manage the transition to college. Drawing upon concepts from institutional theory, the analysis illustrates how pressures from urban policy environments can threaten the viability of a college counseling strategy that has strong positive implications for urban high school students.