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This paper outlines three functions that high school diplomas signal in our schools and in students’ lives, and the tensions among them. It also explores what it says is a false dichotomy between college and career training preparation and how that false choice is stymieing both efforts. The brief ultimately argues for revamped career and technical education programs, increased rigor in academic courses, regular measurement of student competency, and improved data collection and reporting on the range of short-term and long-term student outcomes that states should be, but often are not, tracking—from reading proficiency to job earnings and college degree attainment.