Engaging in activities that make people feel authentic or real is typically associated with a host of positive psychological and physiological outcomes (i.e., being authentic serves to increase well-being). In the current study, we tested the idea that authenticity might have a dark side among people engaged in an addictive or risky behavior (gambling). To test this possibility, we assessed gamblers (N = 61) who were betting on the National Hockey League playoff games at a sports bar. As predicted, people who felt authentic when gambling reported behavior associated with problem gambling (high frequency of betting) as well as problematic play (a big monetary loss and a big monetary win). Moreover, such behavior and gambling outcomes were particularly high among people who were motivated to gamble for the purpose of enhancement. The interaction of feeling authentic when betting and gambling for purposes of enhancing positive emotions proved especially troublesome for problematic forms of play. Implications of authenticity as a potential vulnerability factor for sports betting and other types of gambling are discussed.