Work-based learning interventions, particularly cooperative education, are a viable way to support the post-high school transition process, enhance work-related cognitive development, and increase the occupational engagement of at-risk youth. Using propensity score matching to analyze data from the Educational Longitudinal Study of 2002 (ELS:2002), the impact of participation in cooperative education on two indicators of postsecondary transition readiness, including postsecondary education plans right after high school and importance placed on work, were examined for students deemed at risk of high school failure. Participation in cooperative education had a significant positive effect on at-risk students' postsecondary education plans right after high school. However, no significant effect was detected for the importance students placed on work. (Contains 7 tables and 4 figures.)