Research on the effectiveness of age-friendly organizational practices tends to focus on older employees’ perceptions of these. Drawing on perceptual congruence and psychological contract theory, we hypothesize that leaders’ perceptions of these organizational practices are relevant as well. Specifically, we argue that (dis)agreement between leaders’ and older employees’ perceptions (i.e., perceptual (in)congruence) of organizational practices related to age-friendly organizational climate, management, and work design plays a role in older employees’ well-being. Polynomial regression and response surface analysis were applied to a dyadic sample of 484 older employees and their leaders from 100 diverse organizations. Results reveal that leader-employee perceptual congruence on high levels of perceived age-friendly work design was related to higher employee well-being. By contrast, older employees’ well-being was lower when leaders evaluated the three age-friendly organizational practices higher than their older employees. Our findings suggest that further theoretical consideration of the role of leader-employee perceptual (in)congruence for aging workforces is needed, and that scholars and organizations should acknowledge the relevance and interplay of different stakeholders’ perceptions within an organization.