Work during the preretirement years is a vital component of long-term wellbeing, especially with life expectancy increasing and the burden of saving for retirement shifting heavily toward workers. Employment experiences at midlife set the stage for the quality of transitions into old age and retirement. Middle-aged individuals without a strong attachment to the workforce face a future of economic vulnerability, and the stakes at this point in the life course are especially high. Though researchers often focus on contemporaneous correlates of labor force attachment, such studies ignore the potential importance of the skills that individuals develop earlier in life that prepare them for work across the life course. This study takes advantage of the recent midlife follow-up of the High School and Beyond (1980) sophomore cohort to examine how the prelabor market skills of a cohort who transitioned to adulthood amid vast technological transformation in the labor market are related to employment over thirty years later, at midlife. Specifically, this study investigates the role of high school coursework in promoting long-term labor force attachment, with a focus on career and technical education.