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Organized after-school programs have garnered increasing attention as critical contexts for youth development. Despite this potential, research on the determinants of program quality for high school (HS) youth is scarce. The present study addresses this issue using case studies from two of the most effective apprenticeships evaluated as part of a mixed-method randomized controlled trial of After School Matters in Chicago, perhaps the largest single-city after-school program for HS youth in the country. Findings contrast the mechanisms through which each apprenticeship impacted participants’ marketable job skills, an important outcome for HS youth. The paper also examines implications of the two models for improving the quality of other after-school programs that aim to support work readiness.