Researchers have become increasingly interested in the strategic value of transparency in corporate social responsibility (CSR) communication in recent years. However, transparency research in CSR communication is still scarce. In particular, little research has examined whether the effects of transparency may depend on contextual factors, such as whether an organization is associated with a stigmatized industry. Grounded on legitimacy theory, this experiment examined the effect of CSR messages on supportive communication intent, purchase intent, and skepticism. Results reveal a main effect of transparency on purchase intent and a main effect of stigmatization on skepticism. Most importantly, there was an interaction, such that a higher level of transparency reduced skepticism when a more stigmatized industry was involved. The results contribute to further contextualizing transparency and CSR research.