The efficacy of diversity training is one of the most debated topics in organizational psychology. On one hand, some scholars suggest that diversity training has limited impact and is not generally effective at leading to behavioral or workplace changes (Dobbin & Kalev, 2018; Forscher et al., 2019). On the other hand, other scholars conclude diversity training can be quite successful under the right circumstances (Bezrukova et al., 2016; Kalinoski et al., 2013). There seems to be universal agreement in the literature, however, that more empirical research on this topic is needed. The current study serves this purpose by focusing on one often overlooked aspect of diversity training – trainer characteristics. Given that training is often delivered online (a trend that is particularly on the rise with the historic COVID-19 pandemic-related transition to remote meetings) and several trainers often appear within a training module, this dissertation tests the impact that various race combinations of two trainers could have on trainees’ diversity training-related reactions, learning, and transfer of training, specifically through perceptions of legitimacy and psychological safety. As predicted, trainer race was significantly associated with perceptions of legitimacy; that is, mixed-race trainer pairs were perceived as higher in legitimacy than White-trainer pairs. There was also partial support for the indirect and conditional indirect effects of legitimacy, psychological safety, and trainee race on the relationship between trainer race and diversity training outcomes but only under certain conditions. Implications of these findings and recommendations for future research are discussed.