In the field of emotion regulation, theory has called for examination of the role of context in moderating the effects of different regulatory strategies, but empirical research is lacking. The current study aimed to empirically examine whether context moderates the social appraisals made of targets who either expressed their emotions or used expressive suppression. We recruited actors to either express or suppress anger or happiness and showed recordings of these actors to 816 American participants via Amazon Mechanical Turk, along with a text-based manipulation of context. We predicted that, when the emotion matched the context (e.g., happiness in a comfort context), expressive targets would receive more positive appraisals than suppressive targets, but that when the emotion did not match the context (e.g., happiness in a conflict context), expressive targets would receive more negative appraisals than suppressive targets. Results showed that targets who expressed happiness in a comfort condition were seen as more warm, competent, appropriate and effective, possessed greater leadership ability and elicited a greater desire to affiliate than targets who suppressed happiness, but that these relationships were attenuated in the conflict context, to the point of nonsignificance for leadership and effectiveness, and reversal for appropriateness. Targets who expressed anger received lower ratings on all social appraisals compared to targets who suppressed anger; these effects were only moderated for appropriateness and effectiveness, where the effects were attenuated in the conflict condition. Explanations for these findings are discussed, along with their implications, both practical and with regard to future research.