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Previous work has studied how career and technical education (CTE) strengthens the connection between school and work to prepare students for future employment, but we do not have a full understanding of how this varies with economic context. We consider how salient features of the subprime mortgage crisis of 2007-10 affected high school graduation and college enrollment through coursetaking. Results suggest that exposure to high-cost mortgages and home value declines had small, positive indirect effects through academic courses. They also indicate that foreclosures had small, negative indirect effects for CTE concentrators through CTE courses. We interpret these patterns as students making stronger investments coursetaking, schools insulating students from economic context, and higher achieving students sorting out of CTE.