--- - |2 Abstract Research indicates that leaders who engage in upward ingratiation, a specific form of impression management, develop positive relationships with their bosses, which in turn enhances leaders’ chances of achieving success at work. However, a more complete understanding of leaders’ ingratiation requires recognition that leaders have multiple audiences and that there may be negative unintended consequences of this behavior to at least one of these audiences. Specifically, upward ingratiation may reduce subordinates’ willingness to contribute to the organization through effective performance because it diminishes relationship quality between leaders and subordinates. To explore this issue, we develop and test a multilevel model that contrasts effects of leaders’ upward ingratiation on leader‐ and subordinate‐level outcomes through the quality of social exchange in the corresponding relationship. We test our predictions by conducting a multiwave, multisource field study with a sample of 91 leaders, 91 bosses, and 215 subordinates in South Korea. Our findings reveal that upward ingratiation is positively associated with indicators of leaders’ intrinsic and extrinsic success because it enhances leader–boss exchange quality (LLX). In contrast, leaders’ upward ingratiation negatively influences subordinates’ job performance because it diminishes leader–subordinate exchange quality (LMX). We also find that subordinates’ perceptions of leaders’ political skill mitigate the negative indirect relationship between upward ingratiation and subordinates’ job performance via LMX quality, and that our hypotheses apply to ingratiation but not to other forms of impression management. We discuss the theoretical and practical implications of our findings in relation to ingratiation specifically and to impression management more generally. - Personnel Psychology, EarlyView.