Today, it is becoming increasingly common for companies to harness the spirit of play in order to increase worker engagement and improve organizational performance. This paper examines the ethics of play in a business context, focusing specifically on the phenomenon of workplace gamification. While critics highlight ethical problems with gamification, they also advocate for more positive, transformative, and life-affirming modes of organizational play. Gamification is ethical, on this view, when it allows users to reach a state of authentic happiness or eudaimonia. The underlying assumption, here, is that the ‘magic circle’ of play—a sphere that exists entirely for its own sake—should be protected in order to secure meaningfulness at work. However, we argue that this faith in play is misguided because play, even at its most autotelic, is ethically ambivalent; it does not lead inexorably to virtuous work environments, but may in fact have an undesirable impact on those who are playing. Our study thus contributes to research on the ‘dark side’ of organizational play, a strand of scholarship that questions the idea that play always points toward the good life.