Individuals with Social Anxiety Disorder (SAD) have difficulty engaging in social situations because their actions are predicated on minimizing the subjectively biased high potential for rejection. That is, individuals with SAD frequently perceive social situations as challenging, and their performance as subpar. Yet when individuals perceive themselves as succeeding in challenging situations, they typically report these situations as enjoyable and rewarding. This subjective experience of succeeding in a challenging situation has been studied as flow (Csikszentmihalyi, 1975; 2000). Thirty-three adults with SAD and 34 matched healthy controls completed a baseline assessment, along with daily and experience sampling entries for 14 days. Results were analyzed using three-level generalized linear mixed effects models, with observations nested within days, nested within participants. Although individuals with and without SAD experienced the same frequency of flow in daily life, social situations led to proportionally more flow in participants with SAD than healthy controls. Both results were unexpected, and reasons for them are explored at length. Several experiential variables (positive emotions during and importance ascribed to the event) predicted the probability of flow during each situation. These results offer intervention-relevant suggestions for how individuals may benefit from seeking out challenging situations that offer maximal rewards.