The Wisconsin Card Sorting Test (WCST) evaluates a subject's ability to shift to a new pattern of behavior in response to the presentation of unexpected negative feedback. The present study introduces a novel version of the traditional WCST by integrating a probabilistic component into its traditional rule shifting to add uncertainty to the task, as well as the option to forage for information during any particular trial. These changes transformed a task that is trivial for neurotypical individuals into a challenging environment useful for evaluating biases and compensatory strategizing. Sixty subjects performed the probabilistic WCST at four uncertainty levels to determine the effect of uncertainty on subject performance and strategy. Results revealed that increasing the level of uncertainty during a run of trials correlated with a reduction in rational strategizing in favor of both random choice and information foraging, evoking biases and suboptimal strategies such as satisfaction of search, negativity bias, and probability matching.