Economic recessions raise unemployment risk and depress wages, leaving especially lasting effects on workers who experience unemployment in weak labor markets. Using NLSY data, I show that these workers systematically land in fragile, short-lived jobs, with greater likelihood of both switching employers and returning to unemployment. To interpret these patterns, I build a search-and-matching model in which risk-neutral firms enter long-term relationships with risk-averse workers while both sides learn match quality gradually. Weaker outside options in recessions lead workers to accept contracts with lower wages and less insurance, making separations into both other jobs and unemployment more frequent when matches are inferred to be of low quality as new information arrives. Calibrating the model to well-established business cycle facts delivers realistic scarring effects of recessions on workers, with persistent impacts on both wages and separation rates. From firms’ perspective, the flip side is a highly volatile user cost of labor: hiring in recessions is cheaper both because wages are lower at entry and throughout the match, and because low-quality matches are ended more readily.