Working memory (WM) is the cognitive construct responsible for maintaining and processing information. Despite the fact that WM permeates nearly every aspect of daily life, the current research on the relationship between WM and metacognitive ability is sparse and inconclusive. In the present study, we were interested in using WM capacity to predict an individual’s perception of difficulty in a category task. We hypothesized that higher WM capacity would allow an individual to more easily complete the task and, subsequently, perceive the task as easier. To test this hypothesis, participants were presented with everyday words and given opportunities for trial-and-error-based learning about to which of three novel categories each word belonged. Next, participants completed two counterbalanced measures of WM, R-span and O-span tasks. Finally, participants were presented with a novel transfer task and a questionnaire that measured strategy usage and perceived task difficulty. Participants were assigned to high and low WM groups based on a median split of the combination of R-span and O-span scores. Preliminary results are consistent with our hypothesis. Individuals in the high WM group rated the task as less difficult than participants in the low WM group. Additionally, the high WM group also had higher accuracy scores than the low WM group on the final trial of the category learning task. These findings have important implications for education. If WM capacity really does influence actual and perceived performance in cognitively demanding situations, manipulating WM load in the classroom could help facilitate success for all students.