We challenge the intuitive belief that greater leader sensitivity is always associated with desirable outcomes for employees and organizations. Specifically, we argue that followers’ idiosyncratic desires for, and perceptions of, leader sensitivity behaviors play a key role in how followers react to their leader’s sensitivity. Moreover, these resulting affective experiences are likely to have important consequences for organizations, specifically as they relate to employee counterproductive work behavior (CWB). Drawing from supplies-values (S-V) fit theory and the stressor-emotion model of CWB, the current study focuses on the affective and behavioral consequences of fit between subordinates’ ideal leader sensitivity behavior preferences and subordinates’ perceptions of their actual leader’s sensitivity behaviors. Polynomial regression analyses reveal that congruence between ideal and actual leader sensitivity influences employee negative affect and, consequently, engagement in counterproductive work behavior.