The current research found that participants who had previously endured an emotionally distressing event (e.g., bullying) more harshly evaluated another person’s failure to endure a similar distressing event compared with participants with no experience enduring the event or those currently enduring the event. These effects emerged for naturally occurring (Studies 1, 3, and 4) and experimentally induced (Study 2) distressing events. This effect was driven by the tendency for those who previously endured the distressing event to view the event as less difficult to overcome (Study 3). Moreover, we demonstrate that the effect is specific to evaluations of perceived failure: Compared with those with no experience, people who previously endured a distressing event made less favorable evaluations of an individual failing to endure the event, but made more favorable evaluations of an individual managing to endure the event (Study 4). Finally, we found that people failed to anticipate this effect of enduring distress, instead believing that individuals who have previously endured emotionally distressing events would most favorably evaluate others’ failures to endure (Study 5). Taken together, these findings present a paradox such that, in the face of struggle or defeat, the people we seek for advice or comfort may be the least likely to provide it.