Outperforming others may be an ambivalent experience, simultaneously evoking pride and discomfort. Two experiments examined the role of deservingness in reactions to being an upward comparison target. Study 1 took place online and experimentally manipulated deservingness by modifying a self-report measure of Sensitivity about Being the Target of a Threatening Upward Comparison (STTUC). Participants predicted more distress and less positive affect under conditions of undeserved (vs. deserved) success; several individual difference variables moderated these effects. Study 2 systematically varied a confederate’s effort to manipulate the perceived deservingness of an outperformed person. Participants were especially likely to downplay their score in the presence of a confederate who appeared to work hard on a task but nevertheless performed poorly. Collectively, findings suggest that people respond most strongly to STTUC when a mismatch exists between deservingness and outcomes.