The poor success rates of students with learning disabilities transitioning to postsecondary education signal that special education transition services, as currently delivered, are failing to prepare students adequately for the demands and expectations they face in college. To date, transition research has provided limited guidance for IEP team members and other stakeholders charged with preparing students with learning disabilities for success in higher education. Furthermore, existing literature is nearly silent on the process of postsecondary education transition service decision-making, and team member understanding of college readiness. I use constructivist grounded theory and semi-structured interviews to explore the question, “How do IEP team members and related stakeholders conceptualize and operationalize college readiness for students with learning disabilities whose postsecondary goals include college?” My sample consists of representatives from each role on a high school IEP team for a student with a learning disability, and professors and disability services staff from a local community college. Findings reveal that stakeholders’ conceptions of what it means to be ready for college are largely aligned, but they describe student preparation that is neither explicit, formalized, nor coordinated. System limitations produce gaps between conceptions of readiness and student preparation, and between respective efforts at preparation across stakeholders. The implications of this study include increased focus on transition-related professional development, and administrative support for service coordination within secondary settings and between secondary and postsecondary settings. Recommendations also call for stakeholders to examine system limitations, including those stemming from special education policies that undermine operationalization of readiness.