Compared to the mass market, luxury brands face unique challenges when it comes to brand authenticity. We shed light on the nature of authenticity in the realm of luxury brands and the resulting challenges. More specifically, we show that consumers resort to indexical, iconic, and existential cues when judging luxury brands’ authenticity. Further, we elaborate on four brand authenticity dimensions and discuss them in a luxury context: continuity, credibility, integrity, and symbolism. We then suggest management activities that might drive or hinder luxury brand authenticity perceptions (e.g., creative leadership, selling the dream factor, user creation, and employee behavior) by arguing that challenges mostly arise through the combination of the four authenticity dimensions with the imminent characteristics of luxury brands (e.g., agency and exclusiveness) that indicate otherwise than these dimensions do. Finally, we derive further research avenues to better understand and handle the complexities of authenticity for future luxury branding.