Varying understandings of college readiness currently exist, as do expectations for what the role of schools and parents should be in helping increase college readiness among students. This case study sheds light on how conceptualizations of and expectations related to college readiness compare among students and teachers at three racially and economically diverse Texas high schools. Two research questions guided the study: 1) How do teachers and student understandings of college readiness at each individual school align and differ? 2) What were the two stakeholder groups’ perspectives regarding college readiness expectations on their campuses and the practices associated with helping students improve college readiness? As few studies have considered how the perspectives of various stakeholder groups compare when it comes to issues of college readiness, this study responds to this gap in the knowledge base.