There is growing interest among scholars and practitioners in the notion of fun at work. In this paper, we examine “task fun regulation”—a behavioral-affective orientation in which employees self-initiate novel or varied interactions with their tasks to generate or sustain the feeling of fun. Drawing on self-determination and flow theories, we hypothesized that time pressure and work autonomy independently and interactively influence task fun regulation and that task fun regulation subsequently enhances task performance. To test our hypotheses, we conducted two studies with full-time workers employing random experience sampling (n = 135) and a two-wave design using supervisor ratings of performance (n = 249). Support was found for the negative relationship between time pressure and task fun regulation (both studies) and the positive relationship between work autonomy and task fun regulation (Study 2). As expected, the negative effect of time pressure on task fun regulation was buffered by high levels of work autonomy, and there was a positive downstream effect of task fun regulation on task performance. Moreover, the antecedents and consequence were linked as expected, indicated by a moderated indirect effect from task fun regulation's antecedents through to performance. These findings underscore the utility of task fun regulation within organizations by elucidating its instrumental benefits and uncovering constraining and enabling work design features likely to facilitate this behavioral-affective orientation.