A vast research literature is devoted to analyzing causes of and potential remedies for early-career teacher attrition. However, much less attention has been paid to late-career attrition among experienced teachers, which is driven primarily by retirement plan incentives. Although there is some variation across states, it is generally the case that late-career teachers retire at much younger ages than their professional counterparts. Moreover, given the well-documented returns to teaching experience, late-career exits are on average more costly to students in K-12 schools than early-career exits. This study uses structural estimates from a dynamic retirement model to simulate the effect of targeted retention bonuses for senior teachers rated as effective or teaching in high-need fields. While the cost per incremental year of instruction is expensive in the short run, it declines over time. Moreover, because labor supply decisions are forward-looking, a temporary bonus has much smaller effects than a permanent one. These findings highlight the value of stability in policies aimed at extending teachers' careers. Overall our results suggest that carefully-targeted retention bonuses can be useful tool in raising the quality of the teaching workforce and closing achievement gaps.