Research examining the career-related outcomes of ingratiation has produced fairly inconsistent findings. To move the literature forward, we draw on cognitive consistency theory and social influence theory to examine how the moderating roles of organization-based self-esteem (OBSE) and political skill may affect ingratiation as a strategy to enhance an employee’s promotability. In Study 1 involving 92 independent matched subordinate–supervisor dyads from Thailand, we found support for the moderating effect of OBSE such that there was a positive relationship between supervisor-reported ingratiation and self-reported promotability among individuals with high as opposed to low OBSE. These results were replicated in Study 2 using 150 independent matched subordinate–peer–supervisor triads. Results revealed that the relationship between peer-reported ingratiation and supervisor-reported promotability became positive for those employees with high as opposed to low political skill.