Casino hotels have long been stereotypically associated with negative images that induce a perceived misfit between their corporate social responsibility (CSR) initiatives and their core business as gaming operators. Building on the contingency theory of communication strategies, a multilevel design was adopted to investigate the negative consequences of CSR misfit on legitimacy through CSR authenticity. The firm-level moderating effects of two communicational cues, relational genuineness and marketing skepticism, are also examined. In a context of controversial industries, this study fills a research void by investigating corporate-level moderators that buffer the insidious influences of CSR misfit. It enriches the literature on the consequences of company–CSR coherence and elucidates the mediating role authenticity plays in the CSR implementation process. Practical implications for gaming operators are provided, and remedies that casino hotels can use to lessen the negative consequences of stigmatization are suggested.