Do second chances at a high-stakes admission exam yield long-term gains? Leveraging fifteen years of Chilean administrative data and an RDD, we examine the causal effects of retaking on educational and labor market trajectories. Narrowly missing a preferred program cutoff triggers a 44% increase in retaking, leading to substantial score gains (0.27 SD) and improved placement and enrollment chances. However, these immediate gains do not persist. Retakers graduate at the same rate and from programs with similar earnings and employability profiles as their counterfactual peers. Our results suggest that retaking serves as a reshuffling mechanism yielding null net welfare gains.