Although it is well documented that anxious individuals have negative expectations about the future, it is unclear what cognitive processes give rise to this expectancy bias. Two studies are reported that use the Expectancy Task, which is designed to assess expectancy bias and illuminate its basis. This task presents individuals with valenced scenarios (Positive Valence, Negative Valence, or Conflicting Valence), and then evaluates their tendency to expect subsequent future positive relative to negative events. The Expectancy Task was used with low and high trait anxious (Study 1: n = 32) and anxiety sensitive (Study 2: n = 138) individuals. Results suggest that in the context of physical concerns, both high anxious samples display a less positive expectancy bias. In the context of social concerns, high trait anxious individuals display a negative expectancy bias only when negatively valenced information was previously presented. Overall, this suggests that anxious individuals display a less positive expectancy bias, and that the processes that give rise to this bias may vary by type of situation (e.g., social or physical) or anxiety difficulty.