<p>This research investigates how employees and their organizations can regulate work uncertainty to improve individual late-career outcomes. We propose that employees’ approach and avoidance crafting strategies relate positively and negatively, respectively, to key late-career outcomes (i.e., work ability and experiences of successful aging at work) through work uncertainty and that these relationships can be moderated by developmental human resource management practices. We test the conceptual model in two studies with late-career employees from Japan (Study 1) and the United States of America (Study 2). Using a three-wave time-lagged design (<i>N</i> = 883), Study 1 confirms all research hypotheses, demonstrating that developmental human resource management practices significantly enhance the positive effects of approach crafting and weaken the negative effects of avoidance crafting on employees’ late-career outcomes via work uncertainty. Using a six-week weekly diary design (<i>N</i> = 289), Study 2 confirms the indirect effects of approach crafting on late-career outcomes through work uncertainty. Altogether, the findings from the two studies provide new theoretical insights into the fields of work and aging, uncertainty regulation, proactive behaviors, and human resource management. They also suggest implications for improving organizational practices on managing work uncertainty and late career.</p>