This chapter adopts a critical perspective on policymaking in European labor markets before, during, and after the Great Recession. Using extensive analysis of recent policies at the flexibility–security interface, the chapter identifies four key weaknesses in relation to young people: There was an over-reliance on supply-side policies and quantitative targets, reforms were driven by macroeconomic stability goals rather than by a coherent vision for the labor market, reforms focused on a downward pressure on job security and employability despite slack labor demand, and there was limited consideration of the impact of precariousness and career insecurity on young people and their life courses. It is argued that European and national employment policy need to focus on durable and resilient labor markets for young women and men transitioning from school to work in the postcrisis period.