In this study, we sought to understand the contexts, experiences, and needs among a sample of U.S. secondary education stakeholders to inform both a theoretical framework and policy contexts underpinning college and career readiness (CCR). Results confirmed a theoretically constructed framework of academic and non-academic CCR skills, with participants offering descriptions that validated and extended the framework. In addition, participants provided critical understandings of educational contexts in which CCR occurs, with both policy constraints and facilitative influences described. Participants identified strategies, policies, and practices to support student readiness for college and career outcomes. Finally, we provide study limitations and implications for research, policy, and practice.