This study examines the extent to which Fair Trade reputation and fit between this reputation and the communicated Fair Trade message influences consumer skepticism and positive electronic word-of-mouth. The results of two experiments show that previous Fair Trade reputation has a direct and indirect effect, via consumer brand identification, on consumer skepticism. Moreover, the fit between a reputation and the communicated message only seems to affect skepticism when the communicated message is perceived as realistic. In industries with bad Fair Trade reputations (Study 1) fit does not seem to have an effect on skepticism, while fit does influence skepticism in industries with a certain reputation history on Fair Trade (Study 2). Skepticism and consumer brand identification play an important mediating role in the relationship between reputation, fit and consumers’ electronic word-of-mouth intentions. We therefore conclude that communicating Fair Trade initiatives can be a rewarding effort but also seems to be a delicate matter.