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Policymakers and researchers in the U.S. have renewed interest in Career and Technical Education (CTE) as a school-to-work strategy, recognizing its potential to provide youth with industry-recognized credentials and workforce-ready skills. This marks a shift from the “college-for-all” model toward a more inclusive vision of career readiness. This study uses comparative qualitative content analysis of three major federal policies: ESSA, WIOA, and Perkins V, to examine how school-to-work transitions are treated within education policy frameworks. Findings reveal both contradictions and complementarities across policy goals and governance. While all three aim to support youth transitions, they show limited integration and coherence. The analysis points to the need for stronger alignment across education and workforce systems for workbound youth.