The purpose of this qualitative phenomenological study was to explore Tennessee high school counselors’ and dual enrollment advisors’ perceptions of student readiness for dual enrollment within the context of school, institutional, state, and federal policies as aligned with adolescent development theories in order to inform both policy and practice. Twelve purposely sampled participants from three school districts within the First Tennessee Core Region responded to questions via a recorded phone interview. Participants reflected on the readiness of their students for dual enrollment in the academic, social, and emotional domains. Additionally, participants identified strengths and weaknesses of dual enrollment programs and the Ready Graduateinitiative in Tennessee through the lenses of their school, post-secondary institutions, and their students and shared ideas for the improvement of programs and increasing student readiness.